Novel Insecticides

ABSTRACT

Compounds of formula I 
     
       
         
         
             
             
         
       
     
     wherein the substituents are as defined in claim  1 , and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as agrochemical active ingredients and can be prepared in a manner known per se.

The present invention relates to novel anthranilamide derivatives, to processes for their preparation, to compositions comprising those compounds, and to their use for controlling insects or representatives of the order Acarina.

Anthranilamide derivatives with insecticidal properties are known and described, for example, in WO 01/70671, WO 03/016284, WO 03/015518, WO 03/024222 and WO 04/033468. There have now been found novel anthranilamide derivatives with pesticidal properties, especially for the control of insects and members of the order Acarina.

The present invention accordingly relates to compounds of formula I

wherein each of E and Z, which may be the same or different, represents oxygen or sulfur; A is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; and it being possible for the three- to ten-membered ring system itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇Cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; X is oxygen, NH or C₁-C₄alkyl-N; Y is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; and it being possible for the three- to ten-membered ring system itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃-alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; p is 0 or 1; q is 0 or 1; B is a three- to four-membered ring system which is fully or partially saturated and can contain a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, and it being possible for the three- to four-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; each R₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁ independently is amino, formyl, C₂-C₆cyanoalkenyl, C₂-C₆alkylcarbonylamino, phenylcarbonylamino which can be mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆trialkylsilyl; or each R₁ independently is 2-,3- or 4-pyridylcarbonylamino which can be mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁ independently is C₂-C₆alkoxycarbonylamino, C₂-C₆alkylaminocarbonylamino, C₃-C₆dialkylaminocarbonylamino, C₂-C₆haloalkylcarbonyl or is a group R_(x)ON═C(R_(y))—, wherein R_(x) and R_(y) independently are hydrogen or C₁-C₆alkyl; n is 0, 1, 2, 3 or 4; each of R₂ and R₃, which may be the same or different, represents hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl; or C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino and C₁-C₆alkyl-C₃-C₆cycloalkylamino; D is phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl; or phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; or D is a group

R₄, R₄′, R₁₀, R₁₇, and R₁₉ independently from each other, are hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₅, R₆, R₈, R₁₁, R₁₂, R₁₅, R₁₆ and R₁₈ independently from each other, are C₁-C₆alkyl or C₁-C₆alkyl mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₄alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino or C₃-C₆cycloalkylamino; or are phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl; or are phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₇, R₉, R₁₃ and R₁₄ independently from each other, are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkenyl or C₃-C₆haloalkenyl and agronomically acceptable salts/isomers/enantiomers/tautomers/N-oxides of those compounds, with the exception of the compound 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-methyl-6-(oxiranylmethyl-carbamoyl)-phenyl]-amide.

Compounds I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrose acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C₁-C₄alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as C₁-C₄alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine. Where appropriate, the corresponding internal salts can furthermore be formed. Preferred within the scope of the invention are agrochemically advantageous salts; however, the invention also encompasses salts which have disadvantage for agrochemical use, for example salts which are toxic to bees or fish, and which are employed, for example, for the isolation or purification of free compounds I or agrochemically utilizable salts thereof. Owing to the close relationship between the compounds I in free form and in the form of their salts, for the purposes of the invention the free compounds I or their salts hereinabove and hereinbelow are respectively to be understood as including, where appropriate, the corresponding salts or the free compounds I. The same applies analogously to tautomers of compounds I and salts thereof. In general, the free form is preferred in each case.

The alkyl groups occurring in the definitions of the substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl and their branched isomers. Alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- or polyunsaturated.

Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl.

Haloalkyl groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Suitable haloalkenyl groups are alkenyl groups which are mono- or polysubstituted by halogen, halogen being fluorine, chlorine, bromine and iodine and in particular fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl and 4,4,4-trifluorobut-2-en-1-yl. Among the C₃-C₂₀alkenyl groups which are mono-, di- or trisubstituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

Suitable haloalkynyl groups are, for example, alkynyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and in particular fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluorobut-2-yn-1-yl. Among the alkynyl groups which are mono- or polysubstituted by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.

Alkoxy groups preferably have a preferred chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy.

Alkoxycarbonyl is, for example, methoxycarbonyl (C₂-alkoxycarbonyl), ethoxycarbonyl (C₃-alkoxycarbonyl), propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of from 1 to 6 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl; preferably methylsulfinyl and ethylsulfinyl.

Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl. Alkoxyalkoxy groups preferably have a chain length of from 1 to 8 carbon atoms. Examples of alkoxyalkoxy groups are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy. Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups having a chain length of from 1 to 4 carbon atoms. Alkylaminocarbonyl is, for example, methylaminocarbonyl (C₂-alkylaminocarbonyl) or ethylaminocarbonyl (C₃-aminocarbonyl). Alkoxyalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl. Alkylthioalkyl groups preferably have from 1 to 8 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have from 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Phenyl, also as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl, may be substituted. In this case, the substituents can be in ortho, meta and/or para position. The preferred substituent positions are the ortho and para positions to the ring attachment point.

Examples for B as a optionally substituted three- to four-membered ring system which is fully or partially saturated and can contain a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, are cyclopropyl, methyl-cyclopropyl, cyclopropenyl, cyclobutyl, cyclobutenyl,

According to the present invention, a three- to ten-membered, monocyclic or fused bicyclic ring system which may be partially saturated or fully saturated is, depending of the number of ring members, for example, selected from the group consisting of

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where said cycloalkyl groups for their part may be preferably unsubstituted or substituted by C₁-C₆alkyl or halogen, or is

wherein each R₂₆ is methyl, each R₂₇ and each R₂₈ are independently hydrogen, C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or trifluoromethyl, X₄ is oxygen or sulfur and r=1, 2, 3 or 4.

Where no free valency is indicated in those definitions, for example as in

the linkage site is located at the carbon atom labelled “CH” or in a case such as, for example,

at the bonding site indicated at the bottom left. The second valence for the bivalent ring system of substituent A or Y can be located at any suitable position of the ring.

According to the present invention, a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated is, depending of the number of ring members, for example, selected from the group consisting of

cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, where said cycloalkyl groups for their part may be preferably unsubstituted or substituted by C₁-C₆alkyl or halogen, or is phenyl, benzyl, naphthyl or the following heterocyclic groups: pyrrolyl; pyridyl; pyrazolyl; pyrimidyl; pyrazinyl; imidazolyl; thiadiazolyl; quinazolinyl; furyl; oxadiazolyl; indolizinyl; pyranyl; isobenzofuranyl; thienyl; naphthyridinyl; (1-methyl-1H-pyrazol-3-yl)-; (1-ethyl-1H-pyrazol-3-yl)-; (1-propyl-1H-pyrazol-3-yl)-; (1H-pyrazol-3-yl)-; (1,5-dimethyl-1H-pyrazol-3-yl)-; (4-chloro-1-methyl-1H-pyrazol-3-yl)-; (1H-pyrazol-1-yl)-; (3-methyl-1H-pyrazol-1-yl)-; (3,5-dimethyl-1H-pyrazol-1-yl)-; (3-isoxazolyl)-; (5-methyl-3-isoxazolyl)-; (3-methyl-5-isoxazolyl)-; (5-isoxazolyl)-; (1H-pyrrol-2-yl)-; (1-methyl-1H-pyrrol-2-yl)-; (1H-pyrrol-1-yl)-; (1-methyl-1H-pyrrol-3-yl)-; (2-furanyl)-; (5-methyl-2-furanyl)-; (3-furanyl)-; (5-methyl-2-thienyl)-; (2-thienyl)-; (3-thienyl)-; (1-methyl-1H-imidazol-2-yl)-; (1H-imidazol-2-yl)-; (1-methyl-1H-imidazol-4-yl)-; (1-methyl-1H-imidazol-5-yl)-; (4-methyl-2-oxazolyl)-; (5-methyl-2-oxazolyl)-; (2-oxazolyl)-; (2-methyl-5-oxazolyl)-; (2-methyl-4-oxazolyl)-; (4-methyl-2-thiazolyl)-; (5-methyl-2-thiazolyl)-; (2-thiazolyl)-; (2-methyl-5-thiazolyl)-; (2-methyl-4-thiazolyl)-; (3-methyl-4-isothiazolyl)-; (3-methyl-5-isothiazolyl)-; (5-methyl-3-isothiazolyl)-; (1-methyl-1H-1,2,3-triazol-4-yl)-; (2-methyl-2H-1,2,3-triazol-4-yl)-; (4-methyl-2H-1,2,3-triazol-2-yl)-; (1-methyl-1H-1,2,4-triazol-3-yl)-; (1,5-dimethyl-1H-1,2,4-triazol-3-yl)-; (3-methyl-1H-1,2,4-triazol-1-yl)-; (5-methyl-1H-1,2,4-triazol-1-yl)-; (4,5-dimethyl-4H-1,2,4-triazol-3-yl)-; (4-methyl-4H-1,2,4-triazol-3-yl)-; (4H-1,2,4-triazol-4-yl)-; (5-methyl-1,2,3-oxadiazol-4-yl)-; (1,2,3-oxadiazol-4-yl)-; (3-methyl-1,2,4-oxadiazol-5-yl)-; (5-methyl-1,2,4-oxadiazol-3-yl)-; (4-methyl-3-furazanyl)-; (3-furazanyl)-; (5-methyl-1,2,4-oxadiazol-2-yl)-; (5-methyl-1,2,3-thiadiazol-4-yl)-; (1,2,3-thiadiazol-4-yl)-; (3-methyl-1,2,4-thiadiazol-5-yl)-; (5-methyl-1,2,4-thiadiazol-3-yl)-; (4-methyl-1,2,5-thiadiazol-3-yl)-; (5-methyl-1,3,4-thiadiazol-2-yl)-; (1-methyl-1H-tetrazol-5-yl)-; (1H-tetrazol-5-yl)-; (5-methyl-1H-tetrazol-1-yl)-; (2-methyl-2H-tetrazol-5-yl)-; (2-ethyl-2H-tetrazol-5-yl)-; (5-methyl-2H-tetrazol-2-yl)-; (2H-tetrazol-2-yl)-; (2-pyridyl)-; (6-methyl-2-pyridyl)-; (4-pyridyl)-; (3-pyridyl)-; (6-methyl-3-pyridazinyl)-; (5-methyl-3-pyridazinyl)-; (3-pyridazinyl)-; (4,6-dimethyl-2-pyrimidinyl)-; (4-methyl-2-pyrimidinyl)-; (2-pyrimidinyl)-; (2-methyl-4-pyrimidinyl)-; (2-chloro-4-pyrimidinyl)-; (2,6-dimethyl-4-pyrimidinyl)-; (4-pyrimidinyl)-; (2-methyl-5-pyrimidinyl)-; (6-methyl-2-pyrazinyl)-; (2-pyrazinyl)-; (4,6-dimethyl-1,3,5-triazin-2-yl)-; (4,6-dichloro-1,3,5-triazin-2-yl)-; (1,3,5-triazin-2-yl)-; (4-methyl-1,3,5-triazin-2-yl)-; (3-methyl-1,2,4-triazin-5-yl)-; (3-methyl-1,2,4-triazin-6-yl)-;

wherein each R₂₆ is methyl, each R₂₇ and each R₂₈ are independently hydrogen, C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio or trifluoromethyl, X₄ is oxygen or sulfur and r=1, 2, 3 or 4.

Where no free valency is indicated in those definitions, for example as in

the linkage site is located at the carbon atom labelled “CH” or in a case such as, for example,

at the bonding site indicated at the bottom left.

Compounds of formula I are preferred, wherein R₄′ is hydrogen and each R₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl.

In especially preferred compounds of formula I,

B is a three- to four-membered ring system which is fully or partially saturated, and it being possible for the three- to four-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen.

Preference is given to subgroups of compounds of formula I wherein

a) p and/or q is 0; b) E and/or Z is oxygen; and/or c) R₂ and/or R₃ is hydrogen. X is preferably oxygen, NH; NMe or NEt. Y is preferably C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy.

Special mention should be made of compounds of formula I wherein R₁ is selected from C₁-C₄alkyl, halogen, C₁-C₅haloalkyl, nitro, C₁-C₄alkoxy, C₁-C₄-haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl and C₁-C₄haloalkylsulfonyl, in particular from halogen and C₁-C₆alkyl, preferably selected from methyl and halogen, most preferably selected from methyl and chloro, and n is 1 or 2, preferably 2. Preferred position of R₁ is meta to the group —C(Z)-N(R₃)-A-(X)_(p)—(Y)_(q)—B.

An outstanding group of compounds of formula I comprises those compounds wherein A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene. Preferably A is C₁-C₆alkylene or cyclopropylene, most preferably methylene or cyclopropylene.

In further preferred compounds of formula I, B is cyclopropyl or cyclobutyl, preferably cyclopropyl.

Special emphasis should also be given to compounds of formula I wherein D is a group D₁, wherein R₅ is 2-pyridyl which can be substituted by halogen, preferably which is monosubstituted by chloro at the 3-position of the pyridine ring, R₄′ is hydrogen or halogen, preferably hydrogen and R₄ is halogen preferably chloro and bromo, C₁-C₆haloalkyl preferably trifluoromethyl, C₁-C₄haloalkoxy, preferably 2,2,2-trifluoroethoxy.

Preference is also given to compounds of formula I wherein B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂). In especially preferred compounds of formula I B is cyclopropyl or cyclobutyl which may be substituted by halogen or methyl, in particular by chloro, bromo and methyl; preferably B is cyclopropyl.

In an outstanding group of compounds of formula I the substituents have the following meanings:

n is 2 and one R₁ is C₁-C₄alkyl, preferably methyl, or halogen, preferably chloro, the other R₁ is halogen preferably chloro or bromo; wherein most preferably one R₁ with the meaning C₁-C₄alkyl occupies the ortho position with regard to the group —N(R₂)—C(E)-D. D is a group D₁, wherein R₄′ is hydrogen, R₄ is halogen preferably chloro and bromo, C₁-C₆haloalkyl preferably trifluoromethyl, C₁-C₄haloalkoxy, preferably 2,2,2-trifluoroethoxy and R₅ is 2-pyridyl monosubstituted by halogen, preferably by 3-chloro; R₂ and R₃ are hydrogen; A is C₁-C₆alkylene or a fully saturated bivalent 3- to 6-membered monocyclic ring system, preferably methylene, cyclopropylene or cyclobutylene, most preferably a fully saturated bivalent 3- to 6-membered monocyclic ring system, in particular cyclopropylene or cyclobutylene; p and q are 0; E and Z are oxygen; and B is cyclopropyl or cyclobutyl, preferably cyclopropyl.

The process according to the invention for preparing compounds of formula I is carried out analogously to known processes, for example those described in WO 01/70671, WO 03/016284, WO 03/015518 and WO 04/033468.

The process for the preparation of a compound of formula I or, where appropriate, a tautomer thereof, in each case in free form or in salt form, comprises

a) for the preparation of a compound of formula I, in which R₂ is hydrogen and E and Z are oxygen, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula II

in which R₁, n, and D have the meanings given for formula I in claim 1, or, where appropriate, a tautomer and/or salt thereof with a compound of formula III

HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III),

in which R₃, A, X, Y, p, q and B have the meanings given for formula I, or, where appropriate, with a tautomer and/or salt thereof or, b) for the preparation of a compound of formula I, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula IV

in which R₁, R₂, n, Z and D have the meanings given for the formula I in claim 1; and X₁ is a leaving group, or, where appropriate, a tautomer and/or salt thereof with a compound of formula II

HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III),

in which R₃, A, X, Y, p, q and B have the meanings given for formula I, or, where appropriate, with a tautomer and/or salt thereof or, c) for the preparation of a compound of formula I, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula V

in which R₁, R₂, R₃, n, A, X, Y, Z and B have the meanings given for the formula I in claim 1, or, where appropriate, a tautomer and/or salt thereof with a compound of formula VI

X₂C(═O)D  (VI),

in which D has the meaning given for formula I in claim 1; and X₂ is a leaving group, or, where appropriate, with a tautomer and/or salt thereof; and/or converting a compound of formula I or, where appropriate, a tautomer thereof, in each case in free form or in salt form, into another compound of formula I or, where appropriate, a tautomer thereof, separating an isomer mixture, which can be obtained in accordance with the process, and isolating the desired isomer and/or converting a free compound of formula I or, where appropriate, a tautomer thereof into a salt or a salt of a compound of formula I or, where appropriate, a tautomer thereof into the free compound of formula I or, where appropriate, a tautomer thereof or into another salt.

The compounds of formula II are described in WO 04/111030. The compounds of formulae III and V are novel and especially developed for the preparation of the compounds of formula I and constitute therefore a further embodiment of the present invention. The preferences for the substituents of formula I mentioned above are also valid for the compounds of formulae III and V.

In especially preferred compounds of formula III

R₃ is hydrogen; A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene; p and q are, independently from each other, 0 or 1; X is oxygen, NH; NCH₃ or NC₂H₅; Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy; B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂), preferably B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.

In especially preferred compounds of formula V

R₁ is C₁-C₄alkyl, halogen, C₁-C₅haloalkyl, nitro, C₁-C₄alkoxy, C₁-C₄-haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₂ and R₃ are hydrogen; A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene; p and q are, independently from each other, 0 or 1; X is oxygen, NH; NCH₃ or NC₂H₅; Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy; B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂), preferably B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.

TABLE B Preferred compounds of formula III represented by the formula IIIa: HN(H)-A-(X)_(p)-(Y)_(q)-B (IIIa), Cpd No. A X Y B B1 CH₂ — — cyclopropyl B2 CHMe — — cyclopropyl B3 C(CH₂CH₂) — — cyclopropyl B4 C(CH₂CH₂) — — cyclobutyl B5 CH₂ — — 2,2-dichloro-cyclopropyl B6 CH₂ — — 1-methyl-2,2-dichloro-cyclo-propyl B7 CH₂ — — 2,2-dibromo-cyclopropyl B8 CH₂ — — 1-methyl-2,2-dibromo-cyclo-propyl B9 CH₂ — — 2,2,3,3-tetrafluoro-cyclobutyl B12 CH₂ — — C(SMe)—(CH₂CH₂CH₂) B13 CH₂ — — C(S(O)Me)—(CH₂CH₂CH₂) B14 CH₂ — — C(S(O)₂Me)—(CH₂CH₂CH₂) B15 CH₂ — — cyclobutyl B16 CH₂ — — C(Me)—(CH₂OCH₂) B17 CH₂ — — CH(CMe₂(CH—CH═CMe₂)) B18 CH₂ — — C(CH₂OCH₃)—(CH₂OCH₂) B19 CH₂ — — CH(CH₂O) B20 CHCOOMe — — cyclopropyl B21 CH₂ — CH₂ CH(CH₂—CFCl) B22 CH₂ — CH₂ cyclopropyl B23 CH₂ — — C(Me)—(CH₂CH₂) B24 CH₂ — — CH(CH₂—CMe₂) B25 CH₂ — — CH(CH₂CH₂O) B26 CH₂ — — C(S(O)(NCOCF₃)Me)—(CH₂CH₂CH₂) B27 CH₂ — — C(S(O)(NH)Me)—(CH₂CH₂CH₂) B28 CH₂ — — CH(CMe₂CMe₂) B29 CH₂ — — C(SMe)—(CH₂CH₂) B30 CH₂ — — C(S(O)₂Me)—(CH₂CH₂) B31 CH₂ — — C(CF₃)—(CH₂CH₂) B32 CH₂ — — CH(CH₂—CFCl) B33 CH₂ — — C(S(O)Me)—(CH₂CH₂) B34 CH₂ — — C(S(O)(NCOCF₃)Me)—(CH₂CH₂) B35 CH₂ — — C(S(O)(NH)Me)—(CH₂CH₂) B36 C(CH₂CH₂) — — C(COOEt)—(CH₂CH₂) B37 C(CH₂CH₂) — — C(COOiBr)—(CH₂CH₂) B38 C(CH₂CH₂) — — CH(CH₂—CMe₂) B39 CMe₂ — — cyclopropyl B40 C(CH₂CH₂) — — C(Me)—(CH₂CH₂)

TABLE D Preferred compounds of formula V represented by formula Va: (Va)

Cpd No. R₉₁ R₉₂ A X Y B D1 Me Cl CH₂ — — cyclopropyl D2 Me Cl CHMe — — cyclopropyl D3 Me Cl C(CH₂CH₂) — — cyclopropyl D4 Me Cl C(CH₂CH₂) — — cyclobutyl D5 Me Cl CH₂ — — 2,2-dichloro-cyclopropyl D6 Me Cl CH₂ — — 1-methyl-2,2-dichloro- cyclo-propyl D7 Me Cl CH₂ — — 2,2-dibromo-cyclopropyl D8 Me Cl CH₂ — — 1-methyl-2,2-dibromo- cyclo-propyl D9 Me Cl CH₂ — — 2,2,3,3-tetrafluoro- cyclobutyl D12 Me Cl CH₂ — — C(SMe)-(CH₂CH₂CH₂) D13 Me Cl CH₂ — — C(S(O)Me)-(CH₂CH₂CH₂) D14 Me Cl CH₂ — — C(S(O)₂Me)-(CH₂CH₂CH₂) D15 Me Cl CH₂ — — cyclobutyl D16 Me Cl CH₂ — — C(Me)-(CH₂OCH₂) D17 Me Cl CH₂ — — CH(CMe₂(CH—CH═CMe₂)) D18 Me Cl CH₂ — — C(CH₂OCH₃)-(CH₂OCH₂) D19 Me Cl CH₂ — — CH(CH₂O) D20 Me Cl CHCOOMe — — cyclopropyl D21 Me Cl CH₂ — CH₂ CH(CH₂—CFCl) D22 Me Cl CH₂ — CH₂ cyclopropyl D23 Me Cl CH₂ — — C(Me)-(CH₂CH₂) D24 Me Cl CH₂ — — CH(CH₂—CMe₂) D25 Me Cl CH₂ — — CH(CH₂CH₂O) D26 Me Cl CH₂ — — O(S(O)(NCOCF₃)Me)- (CH₂CH₂CH₂) D27 Me Cl CH₂ — — C(S(O)(NH)Me)- (CH₂CH₂CH₂) D28 Me Cl CH₂ — — CH(CMe₂CMe₂) D29 Me Cl CH₂ — — C(SMe)-(CH₂CH₂) D30 Me Cl CH₂ — — C(S(O)₂Me)-(CH₂CH₂) D31 Me Cl CH₂ — — C(CF₃)-(CH₂CH₂) D32 Me Cl CH₂ — — CH(CH₂—CFCl) D33 Me Cl CH₂ — — C(S(O)Me)-(CH₂CH₂) D34 Me Cl CH₂ — — C(S(O)(NCOCF₃)Me)-(CH₂CH₂) D35 Me Cl CH₂ — — C(S(O)(NH)Me)-(CH₂CH₂) D36 Me Cl C(CH₂CH₂) — — C(COOEt)-(CH₂CH₂) D37 Me Cl C(CH₂CH₂) — — C(COOiDr)-(CH₂CH₂) D38 Me Cl C(CH₂CH₂) — — CH(CH₂—CMe₂) D39 Cl H CH₂ — — cyclopropyl D40 Cl H C(CH₂CH₂) — — cyclopropyl D41 Me H CH₂ — — cyclopropyl D42 Me H C(CH₂CH₂) — — cyclopropyl D43 Me Cl CMe₂ — — cyclopropyl D44 Me Cl C(CH₂CH₂) — — C(Me)-(CH₂CH₂) D45 Me 2-pyridyl CH₂ — — cyclopropyl D47 Me 2-pyridyl C(CH₂CH₂) — — cyclopropyl D48 Me Cl C(CH₂CH₂) — — cyclopropyl D49 Me 3-pyridyl CH₂ — — cyclopropyl D50 Me Cl C(CH₂CH₂) — — cyclopropyl D51 Me Cl C(CH₂CH₂) — — cyclopropyl D52 Me NH₂ C(CH₂CH₂) — — cyclopropyl D53 Me NH₂ CH₂ — — cyclopropyl D54 Me I C(CH₂CH₂) — — cyclopropyl D55 Me Br CH₂ — — cyclopropyl D56 Me Br CH₂ — — cyclopropyl D57 Me Br C(CH₂CH₂) — — cyclopropyl D58 Me Br CH₂ — — cyclopropyl D59 Me Br C(CH₂CH₂) — — cyclopropyl D60 Me NO₂ CH₂ cyclopropyl D61 Me NO₂ C(CH₂CH₂) cyclopropyl D62 Me NO₂ C(CH₂CH₂) cyclopropyl D63 Me NO₂ C(CH₂CH₂) cyclopropyl D64 Me NO₂ C(CH₂CH₂) cyclopropyl D65 Me Cl CH₂ — — cyclobutyl D66 Me Cl CHMe — — cyclobutyl D67 Me Cl CH(CH₂)C — — C(CH₂)₂

Physical data for compounds of formula Va according to Table D:

Compound No. melting point D1 128-129° C. D3 177-178° C.

What has been said above for tautomers and/or salts of compounds I applies analogously to starting materials mentioned hereinabove and hereinbelow with regard to the tautomers and/or salts thereof.

The reactions described hereinabove and hereinbelow are carried out in a manner known per se, for example in the absence or, normally, in the presence of a suitable solvent or diluent or of a mixture of these, the process being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range of from approximately −80° C. to the boiling point of the reaction mixture, preferably from approximately −20° C. to approximately +150° C., and, if required, in a sealed vessel, under reduced, normal or elevated pressure, in an inert gas atmosphere and/or under anhydrous conditions. Especially advantageous reaction conditions can be seen from the examples.

Unless otherwise specified, the starting materials mentioned hereinabove and hereinbelow, which are used for the preparation of the compounds I or, where appropriate, the tautomers thereof, in each case in free form or in salt form, are known or can be prepared by methods known per se, for example in accordance with the information given below.

Variant a)

The reactants can be reacted with each other as such, i.e. without addition of a solvent or diluent, for example in the melt. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. Examples of such solvents or diluents which may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halohydrocarbons such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; esters such as ethyl acetate; ethers such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethyleneglycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; amides such as N,N-di-methylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide.

The reaction is advantageously carried out in a temperature range from approximately −80° C. to approximately +140° C., preferably from approximately −30° C. to approximately +100° C., in many cases in the range between room temperature and approximately +80° C.

Variant b)

Examples of suitable leaving groups X₁ in the compounds IV are hydroxy, C₁-C₈alkoxy, halo-C₁-C₈alkoxy, C₁-C₈alkanoyloxy, mercapto, C₁-C₈alkylthio, halo-C₁-C₈alkylthio, C₁-C₈alkylsulfonyloxy, halo-C₁-C₈alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy and halogen, such as chlorine. Preferred are hydroxy, C₁-C₈alkoxy and chlorine.

The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. Examples of suitable solvents or diluents are of the type described under variant a).

The reaction is advantageously carried out in a temperature range from approximately −80° C. to approximately +140° C., preferably from approximately −20° C. to approximately +100° C., in many cases in the range between room temperature and the reflux temperature of the reaction mixture.

Variant c)

Examples of suitable leaving groups X₂ in the compounds VI are hydroxy, C₁-C₈alkoxy, halo-C₁-C₈alkoxy, C₁-C₈alkanoyloxy, mercapto, C₁-C₈alkylthio, halo-C₁-C₈alkylthio, C₁-C₈alkylsulfonyloxy, halo-C₁-C₈alkylsulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy and halogen, such as chlorine. Preferred are hydroxy and chlorine.

The reactants can be reacted in the presence of a base. Examples of suitable bases for facilitating the detachment of HX₂ are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reactants can be reacted with each other as such, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture of these. Examples of suitable solvents or diluents are of the type described under variant a). If the reaction is carried out in the presence of a base, bases which are employed in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, may also act as solvents or diluents.

The reaction is advantageously carried out in a temperature range from approximately −80° C. to approximately +140° C., preferably from approximately −30° C. to approximately +100° C., in many cases in the range between room temperature and approximately +80° C.

A compound I can be converted in a manner known per se into another compound I by replacing one or more substituents of the starting compound I in the customary manner by (an)other substituent(s) according to the invention.

For example,

-   -   in compounds I, in which R₂ is hydrogen, this hydrogen R₂ can be         replaced by a substituent R₂, which is different from hydrogen;         or     -   in compounds I, in which R₃ is hydrogen, this hydrogen R₃ can be         replaced by a substituent R₃, which is different from hydrogen.

Depending on the choice of the reaction conditions and starting materials which are suitable in each case, it is possible, for example, in one reaction step only to replace one substituent by another substituent according to the invention, or a plurality of substituents can be replaced by other substituents according to the invention in the same reaction step.

Salts of compounds I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

Salts of compounds I can be converted in the customary manner into the free compounds I, acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.

Salts of compounds I can be converted in a manner known per se into other salts of compounds I, acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.

Depending on the procedure or the reaction conditions, the compounds I, which have salt-forming properties can be obtained in free form or in the form of salts.

The compounds I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule; the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and hereinbelow, even when stereochemical details are not mentioned specifically in each case.

Diastereomer mixtures or racemate mixtures of compounds I, in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diasteromers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.

Enantiomer mixtures, such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the diastereomers, from which the desired enantiomer can be set free by the action of suitable agents, for example basic agents.

Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.

It is advantageous to isolate or synthesize in each case the biologically more effective isomer, for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.

The compounds I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

The compounds I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. The active ingredients according to the invention act against all or individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina. The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i.e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, a good activity corresponding to a destruction rate (mortality) of at least 50 to 60%.

Examples of the abovementioned animal pests are:

from the order Acarina, for example, Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp. and Tetranychus spp.; from the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Coleoptera, for example, Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.; from the order Diptera, for example, Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; from the order Heteroptera, for example, Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.; from the order Homoptera, for example, Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Parlatoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; from the order Hymenoptera, for example, Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.; from the order Isoptera, for example, Reticulitermes spp.; from the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiela, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.; from the order Mallophaga, for example,

Damalinea spp. and Trichodectes spp.;

from the order Orthoptera, for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Psocoptera, for example,

Liposcelis spp.;

from the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; from the order Thysanoptera, for example, Frankliniella spp., Hercinothrips spp., Scirtothrips aurantii, Taeniothrips spp., Thrips palmi and Thrips tabaci; and from the order Thysanura, for example, Lepisma saccharina.

The active ingredients according to the invention can be used for controlling, i.e. containing or destroying, pests of the abovementioned type which occur in particular on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.

Suitable target crops are, in particular, cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beet, such as sugar or fodder beet; fruit, for example pomaceous fruit, stone fruit or soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; leguminous crops, such as beans, lentils, peas or soya; oil crops, such as oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa or ground nuts; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or bell peppers; Lauraceae, such as avocado, Cinnamonium or camphor; and also tobacco, nuts, coffee, eggplants, sugarcane, tea, pepper, grapevines, hops, the plantain family, latex plants and ornamentals.

The active ingredients according to the invention are especially suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetable, maize, rice and soya crops. The active ingredients according to the invention are further especially suitable for controlling Mamestra (preferably in vegetables), Cydia pomonella (preferably in apples), Empoasca (preferably in vegetables, vineyards), Leptinotarsa (preferably in potatoes) and Chilo supressalis (preferably in rice).

The term “crops” is to be understood as including also crops that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

The term “crops” is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIA, CryIIB(b1) or Cry9c, or vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsine inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood by δ-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c, or vegetative insecticidal proteins (VIP), for example VIP1, VIP2, VIP3 or VIP3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CryIA(b), are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of CryIIIA055, a cathepsin-D-recognition sequence is inserted into a CryIIIA toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses a CryIA(b) and a CryIIB(b1) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); Boligard I® (cotton variety that expresses a CryIA(c) toxin); Boligard II® (cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CryIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

-   1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31     790 St. Sauveur, France, registration number C/FR/96/05/10.     Genetically modified Zea mays which has been rendered resistant to     attack by the European corn borer (Ostrinia nubilalis and Sesamia     nonagrioides) by transgenic expression of a truncated CryIA(b)     toxin. Bt11 maize also transgenically expresses the enzyme PAT to     achieve tolerance to the herbicide glufosinate ammonium. -   2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31     790 St. Sauveur, France, registration number C/FR/96/05/10.     Genetically modified Zea mays which has been rendered resistant to     attack by the European corn borer (Ostrinia nubilalis and Sesamia     nonagrioides) by transgenic expression of a CryIA(b) toxin. Bt176     maize also transgenically expresses the enzyme PAT to achieve     tolerance to the herbicide glufosinate ammonium. -   3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I′Hobit 27, F-31     790 St. Sauveur, France, registration number C/FR/96/05/10. Maize     which has been rendered insect-resistant by transgenic expression of     a modified CryIIIA toxin. This toxin is Cry3A055 modified by     insertion of a cathepsin-D-protease recognition sequence. The     preparation of such transgenic maize plants is described in WO     03/018810. -   4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de     Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.     MON 863 expresses a CryIIIB(b1) toxin and has resistance to certain     Coleoptera insects. -   5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de     Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02. -   6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7     B-1160 Brussels, Belgium, registration number C/NL/00/10.     Genetically modified maize for the expression of the protein CryI F     for achieving resistance to certain Lepidoptera insects and of the     PAT protein for achieving tolerance to the herbicide glufosinate     ammonium. -   7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de     Tervuren, B-1150 Brussels, Belgium, registration number     C/GB/02/M3/03. Consists of conventionally bred hybrid maize     varieties by crossing the genetically modified varieties NK603 and     MON 810. NK603×MON 810 Maize transgenically expresses the protein     CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts     tolerance to the herbicide Roundup® (contains glyphosate), and also     a CryIA(b) toxin obtained from Bacillus thuringiensis subsp.     kurstaki which brings about tolerance to certain Lepidoptera,     include the European corn borer.

Transgenic crops of insect-resistant plants are also described in BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).

The term “crops” is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called “pathogenesis-related proteins” (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called “pathogenesis-related proteins” (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called “plant disease resistance genes”, as described in WO 03/000906).

Further areas of use of the compositions according to the invention are the protection of stored goods and storerooms and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animals and productive livestock against pests of the mentioned type.

In the hygiene sector, the compositions according to the invention are active against ectoparasites such as hard ticks, soft ticks, mange mites, harvest mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

Examples of Such Parasites are:

Of the order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp. and Phtirus spp., Solenopotes spp. Of the order Mallophagida: Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp. Of the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp. Of the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp. Of the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. Of the order Blattarida, for example Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp. Of the subclass Acaria (Acarida) and the orders Meta- and Meso-stigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp. Of the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The compositions according to the invention are also suitable for protecting against insect infestation in the case of materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and buildings.

The compositions according to the invention can be used, for example, against the following pests: beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. and Dinoderus minutus, and also hymenopterans such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus and Urocerus augur, and termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, and bristletails such as Lepisma saccharina.

The invention therefore also relates to pesticidal compositions such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise—at least—one of the active ingredients according to the invention and which are to be selected to suit the intended aims and the prevailing circumstances.

In these compositions, the active ingredient is employed in pure form, a solid active ingredient for example in a specific particle size, or, preferably, together with—at least—one of the auxiliaries conventionally used in the art of formulation, such as extenders, for example solvents or solid carriers, or such as surface-active compounds (surfactants).

Examples of suitable solvents are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C₈ to C₁₂ of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols such as ethanol, propanol or butanol, glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unexpodized or epoxidized rapeseed, castor, coconut or soya oil, and silicone oils.

Solid carriers which are used for example for dusts and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties, it is also possible to add highly disperse silicas or highly disperse absorbtive polymers. Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are calcite or sand. In addition, a large number of granulated materials of inorganic or organic nature can be used, in particular dolomite or comminuted plant residues.

Suitable surface-active compounds are, depending on the type of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties. The surfactants mentioned below are only to be considered as examples; a large number of further surfactants which are conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.

Suitable non-ionic surfactants are, especially, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids or of alkyl phenols which may contain approximately 3 to approximately 30 glycol ether groups and approximately 8 to approximately 20 carbon atoms in the (cyclo)aliphatic hydrocarbon radical or approximately 6 to approximately 18 carbon atoms in the alkyl moiety of the alkyl phenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol or alkyl polypropylene glycol having 1 to approximately 10 carbon atoms in the alkyl chain and approximately 20 to approximately 250 ethylene glycol ether groups and approximately 10 to approximately 100 propylene glycol ether groups. Normally, the abovementioned compounds contain 1 to approximately 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are, especially, quarternary ammonium salts which generally have at least one alkyl radical of approximately 8 to approximately 22 C atoms as substituents and as further substituents (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethyl-ammonium bromide.

Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surface-active compounds. Examples of suitable soaps are the alkali, alkaline earth or (un-substituted or substituted) ammonium salts of fatty acids having approximately 10 to approximately 22 C atoms, such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which are obtainable for example from coconut or tall oil; mention must also be made of the fatty acid methyl taurates. However, synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates. As a rule, the fatty sulfonates and fatty sulfates are pre-sent as alkali, alkaline earth or (substituted or unsubstituted) ammonium salts and they generally have an alkyl radical of approximately 8 to approximately 22 C atoms, alkyl also to be understood as including the alkyl moiety of acyl radicals; examples which may be mentioned are the sodium or calcium salts of lignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids. This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and a fatty acid radical of approximately 8 to approximately 22 C atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of decylbenzenesulfonic acid, of dibutyl-naphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate. Also possible are, furthermore, suitable phosphates, such as salts of the phosphoric ester of a p-nonylphenol/(4-14)ethylene oxide adduct, or phospholipids.

As a rule, the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of active ingredient and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient. Preferred compositions are composed in particular as follows (%=percent by weight):

Emulsifiable concentrates: active ingredient:   1 to 95%, preferably 5 to 20% surfactant:   1 to 30%, preferably 10 to 20% solvent:   5 to 98%, preferably 70 to 85% Dusts: active ingredient:  0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension concentrates: active ingredient:   5 to 75%, preferably 10 to 50% water:   94 to 24%, preferably 88 to 30% surfactant:   1 to 40%, preferably 2 to 30% Wettable powders: active ingredient:  0.5 to 90%, preferably 1 to 80% surfactant:  0.5 to 20%, preferably 1 to 15% solid carrier:   5 to 99%, preferably 15 to 98% Granulates: active ingredient:  0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%

The compositions can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds I for the preparation of these compositions are also a subject of the invention.

The application methods for the compositions, that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring—which are to be selected to suit the intended aims of the prevailing circumstances—and the use of the compositions for controlling pests of the abovementioned type are other subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.

The compositions according to the invention are also suitable for the protection of plant propagation material, for example seeds, such as fruit, tubers or kernels, or nursery plants, against pests of the abovementioned type. The propagation material can be treated with the compositions prior to planting, for example seed can be treated prior to sowing. Alternatively, the compositions can be applied to seed kernels (coating), either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention.

PREPARATION EXAMPLES Example H1 Preparation of N-(4-chloro-2-methyl-6-[([oxetan-2-ylmethyl]amino)carbonyl]phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide (Compound P25)

Step 1: Preparation of 2-(phtalimidomethyl)oxetane:

A solution of 2-(tosyloxymethyl)oxetane (27 g, 111.4 mmol) (prepared according to A. O. Fitton et al., Synthesis 1987, (12), 1140-2) and potassium phtalimide (20.64 g, 111.4 mmol) in DMF (200 ml) is stirred at a temperature of 120° C. for 18 hours, then evaporated in vacuo. The residue is taken up in ethyl acetate, the organic layer washed with water and brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude solid product (19.8 g, 82%) is used in the next step without further purification.

Step 2: Preparation of 2-aminomethyloxetane:

To a solution of 2-(phtalimidomethyl)oxetane (the product of step 1) (19 g, 87.5 mmol) in ethanol (250 ml) is added hydrazine hydrate (6.56 g, 131.2 mmol) and the reaction mixture is heated to reflux for 30 minutes. The resulting precipitates are filtered off, a small amount of Raney Ni (W-2) added to the filtrate, and the mixture further refluxed for 1.5 hours. The inorganic materials are filtered off, and the filtrate was concentrated carefully under reduced pressure. The residue is distilled in vacuo to give a colorless liquid (3.63 g, ˜47%), b.p. 55-60° C./30 mbar. Contaminated with ethanol and DMF, the product is used in the next step without further purification.

Step 3: Preparation of Compound P25:

To a solution of 6-chloro-2-[1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (200 mg, 0.45 mmol) (prepared according to WO 02/48115, example 2D) in tetrahydrofurane (4 ml), is added 2-aminomethyloxetane (the product of step 2) (79 mg, 0.91 mmol), and the mixture is heated to reflux for 30 minutes. The solution is allowed to cool to ambient temperature and the solvent evaporated in vacuo. The residue is purified by prep. HPLC (hexane/ethyl acetate gradient on LiChrospher Si 60, Merck NW25 column) to afford 180 mg (71%) of the title compound as a white solid. [¹H-NMR (CDCl₃): 10.21 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.41 (m, 1H), 7.32 (s, 1H), 7.29 (m, 2H), 6.63 (m, 1H), 4.98 (m, 1H), 4.68 (m, 1H), 4.48 (m, 1H), 3.71 (m, 1H), 3.59 (m, 1H), 2.68 (m, 1H), 2.43 (m, 1H), 2.19 (s, 3H); MS (electrospray ES+): 528, 530 ((M+H)⁺)].

Preparation of the Intermediate bicyclopropyl-1-ylamine:

93.2 ml (328 mmol) Ti(OiPr)₄ is added to a solution of 20 g (298 mmol) cyclopropane carbonitrile in 300 ml ether. The solution is cooled down to a temperature of −78° C. and 199 ml (596 mmol) ethylmagnesium bromide solution (3 M in ether) is slowly added. After 10 min at −78° C., the slurry is allowed to warm up to ambient temperature and stirred for 1 hour. 84.6 g (595 mmol) BF₃.OEt₂ is added and the mixture is stirred at ambient temperature for 18 hours. To this mixture, 600 ml NaOH 2N is slowly added at a temperature of 0° C. The organic phase is separated and extracted with 600 ml HCl 2N. The water phase is evaporated and the residue is triturated in ether to afford 30.9 g (78%) of the title compound as an hydrochloride salt.

The compounds listed in the following Tables P, P′ and A can be prepared analogous to the procedures described above (m.p.=melting point in ° C.): If no definition for substituent X is given, then p is 0, if X is a substituent, then p is 1. If no definition for substituent Y is given, then q is 0, if Y is a substituent, then q is 1. The group C(CH₂CH₂) for the substituent A means cyclopropyl with two free valences:

Designations for substituent B like CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)-(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)-(CH-MeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂) define cyclic rings. For example, CH(CH₂O) is

C(Me)-(CH-MeO) is

and

C(Me)-(CHMe-S(O)₂CH₂) is

TABLE P Compounds of formula Ia: (Ia)

Cpd No. R₉₁ R₉₂ R₉₃ A X Y B Phys. Data P1 Me Cl CF₃ CH₂ — — cyclopropyl MS (−ve) 510 (M − 1)⁻ P2 Me Cl CF₃ CHMe — — cyclopropyl MS (+ve) 525 (M⁺) MS (−ve) 524 (M − H)⁻ P3 Me Cl CF₃ C(CH₂CH₂) — — cyclopropyl MS (−ve) 536 (M − H)⁻ P4 Me Cl CF₃ C(CH₂CH₂) — — cyclobutyl MS (−ve) 550 (M − H)⁻ P5 Me Cl CF₃ CH₂ — — 2,2-dichloro- MS (−ve) cyclopropyl 580 (M − H)⁻ P6 Me Cl CF₃ CH₂ — — 1-methyl-2,2- MS (−ve) dichloro-cyclo- 594 (M − H)⁻ propyl P7 Me Cl CF₃ CH₂ — — 2,2-dibromo- MS (−ve) cyclopropyl 668 (M − H)⁻ P8 Me Cl CF₃ CH₂ — — 1-methyl-2,2- MS (−ve) dibromo-cyclo- 682 (M − H)⁻ propyl P9 Me Cl CF₃ CH₂ — — 2,2,3,3- MS (−ve) tetrafluoro- 597 (M − H)⁻ cyclobutyl P10 Me Cl Br CH₂ — — cyclopropyl 218-220° C. P11 Me Cl Cl CH₂ — — cyclopropyl 218-219° C. P12 Me Cl CF₃ CH₂ — — C(SMe)- MS (ES+) (CH₂CH₂CH₂) 572/574 (M + H)⁺ P13 Me Cl CF₃ CH₂ — — C(S(O)Me)- 223-224° C. (CH₂CH₂CH₂) P14 Me Cl CF₃ CH₂ — — C(S(O)₂Me)- >250° C. (CH₂CH₂CH₂) MS (ES+) 604/606 (M + H)⁺ P15 Me Cl CF₃ CH₂ — — cyclobutyl 206-208° C. P16 Me Cl CF₃ CH₂ — — C(Me)- 201-203° C. (CH₂OCH₂) P17 Me Cl CF₃ CH₂ — — CH(CMe₂(CH—CH═CMe₂)) 178-179° C. P18 Me Cl CF₃ CH₂ — — C(CH₂OCH₃)- 190-192° C. (CH₂OCH₂) P19 Me Cl CF₃ CH2 — — CH(CH₂O) MS (ES+) 514/516 (M + H)⁺ P20 Me Cl CF₃ CHCOOMe — — cyclopropyl MS (ES−) 568 (M − H)⁻ P21 Me Cl CF₃ CH₂ — CH₂ CH(CH₂—CFCl) 154-156° C. P22 Me Cl CF₃ CH₂ — CH₂ cyclopropyl 122-124° C. P23 Me Cl CF₃ CH₂ — — C(Me)-(CH₂CH₂) 208-210° C. P24 Me Cl CF₃ CH₂ — — CH(CH₂—CMe₂) MS (ES+) 540/542 (M + H)⁺ P25 Me Cl CF₃ CH₂ — — CH(CH₂CH₂O) MS (ES+) 528/530 (M + H)⁺ P26 Me Cl CF₃ CH₂ — — C(S(O)(NCOCF₃)Me- MS(ES+) (CH₂CH₂CH₂) 699/701 (M + H)⁺ P27 Me Cl CF₃ CH₂ — — C(S(O)(NH)Me)- MS (ES+) (CH₂CH₂CH₂) 603/605 (M + H)⁺ P28 Me Cl CF₃ CH₂ — — CH(CMe₂CMe₂) 206-208° C. P29 Me Cl CF₃ CH₂ — — C(SMe)-(CH₂CH₂) 214-215° C. P30 Me Cl CF₃ CH₂ — — C(S(O)₂Me)- 212-214° C. (CH₂CH₂) P31 Me Cl CF₃ CH₂ — — C(CF₃)-(CH₂CH₂) 198-200° C. P32 Me Cl CF₃ CH₂ — — CH(CH₂—CFCl) 228-229° C. P33 Me Cl CF₃ CH₂ — — C(S(O)Me)- 212-214° C. (CH₂CH₂) P34 Me Cl CF₃ CH₂ — — C(S(O)(NCOCF₃)Me)- 210-212° C. (CH₂CH₂) P35 Me Cl CF₃ CH₂ — — C(S(O)(NH)Me)- 208-210° 0.C (CH₂CH₂) P36 Me Cl CF₃ C(CH₂CH₂) — — C(COOEt)- 212-213° C. (CH₂CH₂) P37 Me Cl CF₃ C(CH₂CH₂) — — C(COOiPr)- 215-217° C. (CH₂CH₂) P38 Me Cl CF₃ C(CH₂CH₂) — — CH(CH₂—CMe₂) MS (ES+) 566/568 (M + H)⁺ P39 Cl H CF₃ CH₂ — — cyclopropyl 222-223° C. P40 Cl H CF₃ C(CH₂CH₂) — — cyclopropyl 233-235° C. P41 Me H CF₃ CH₂ — — cyclopropyl 183-185° C. P42 Me H CF₃ C(CH₂CH₂) — — cyclopropyl 232-233° C. P43 Me Cl CF₃ CMe₂ — — cyclopropyl 248-249° C. P44 Me Cl CF₃ C(CH₂CH₂) — — C(Me)-(CH₂CH₂) MS (ES+) 552/554 (M + H)⁺ P45 Me 2-pyridyl CF₃ CH₂ — — cyclopropyl 220-221° C. P46 Me Cl OCH₂CF₃ CH₂ — — cyclopropyl 174-176° C. P47 Me 2-pyridyl CF₃ C(CH₂CH₂) — — cyclopropyl 224-225° C. P48 Me Cl OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 168-170° C. P49 Me 3-pyridyl CF₃ CH₂ — — cyclopropyl 214-215° C. P50 Me Cl Cl C(CH₂CH₂) — — cyclopropyl 222-225° C. P51 Me Cl Br C(CH₂CH₂) — — cyclopropyl 229-232° C. P52 Me NH₂ CF₃ C(CH₂CH₂) — — cyclopropyl 252-254° C. P53 Me NH₂ CF₃ CH₂ — — cyclopropyl 232-234° C. P54 Me I OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 235-236° C. P55 Me Br CF₃ CH₂ — — cyclopropyl 180-185° C. P56 Me Br Cl CH₂ — — cyclopropyl 215-224° C. P57 Me Br CF₃ C(CH₂CH₂) — — cyclopropyl 135-139° C. P58 Me Br Br CH₂ — — cyclopropyl 220-225° C. P59 Me Br Cl C(CH₂CH₂) — — cyclopropyl 178-182° C. P60 Me NO₂ CF₃ CH₂ cyclopropyl 195-199° C. P61 Me NO₂ CF₃ C(CH₂CH₂) cyclopropyl 215-217° C. P62 Me NO₂ Br C(CH₂CH₂) cyclopropyl 209-215° C. P63 Me NO₂ Cl C(CH₂CH₂) cyclopropyl 213-216° C. P64 Me NO₂ OCH₂CF₃ C(CH₂CH₂) cyclopropyl 218-221° C. P65 Me Cl CF₃ CH₂ — — cyclobutyl MS (ES+) 526 (MH⁺) MS (ES−) 524 (M − H)⁻ P66 Me Cl CF₃ CHMe — — cyclobutyl MS (ES+) 540 (MH⁺) MS (ES−) 538 (M − H)⁻ P67 Me Cl CF₃ CH(CH₂)C — — C(CH₂)₂ 157-163° C. P68 Me Cl CF₃ CH(CH₂)C — — C(CH₂)₃ 143-145° C.

TABLE P′ Compounds of formula Ia′: (Ia′)

Cpd No. R₉₁ R₉₂ R₉₃ A X Y B Phys. Data P69 Me Cl OCH₂CF₃ CH₂ — — cyclopropyl 174-181° C. P70 Me Cl OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 150-154° C. P71 Me I OCH₂CF₃ C(CH₂CH₂) — — cyclopropyl 180-184° C. P72 Me I OCH₂CF₃ CH₂ — — cyclopropyl 205-211° C.

The examples which follow are intended to illustrate the invention and show preferred compounds of formula I. Me means the methyl group. Et means the ethyl group. tBu is tert.-butyl. If no definition for substituent X is given, then p is 0, if X is a substituent, then p is 1. If no definition for substituent Y is given, then q is 0, if Y is a substituent, then q is 1.

TABLE A Compounds of formula Ia: (Ia)

Comp. No. R₉₁ R₉₂ R₉₃ A X Y B A.1.1 Me Br CF₃ CH₂ — — cyclo- propyl A.1.2 Me Br CF₃ CHMe — — cyclo- propyl A.1.3 Me Br CF₃ CMe₂ — — cyclo- propyl A.1.4 Me Br CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.5 Me F CF₃ CH₂ — — cyclo- propyl A.1.6 Me F CF₃ CHMe — — cyclo- propyl A.1.7 Me F CF₃ CMe₂ — — cyclo- propyl A.1.8 Me F CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.9 Me I CF₃ CH₂ — — cyclo- propyl A.1.10 Me I CF₃ CHMe — — cyclo- propyl A.1.11 Me I CF₃ CMe₂ — — cyclo- propyl A.1.12 Me I CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.13 Cl Cl CF₃ CH₂ — — cyclo- propyl A.1.14 Cl Cl CF₃ CHMe — — cyclo- propyl A.1.15 Cl Cl CF₃ CMe₂ — — cyclo- propyl A.1.16 Cl Cl CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.17 Cl Br CF₃ CH₂ — — cyclo- propyl A.1.18 Cl Br CF₃ CHMe — — cyclo- propyl A.1.19 Cl Br CF₃ CMe₂ — — cyclo- propyl A.1.20 Cl Br CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.21 Cl F CF₃ CH₂ — — cyclo- propyl A.1.22 Cl F CF₃ CHMe — — cyclo- propyl A.1.23 Cl F CF₃ CMe₂ — — cyclo- propyl A.1.24 Cl F CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.25 Cl I CF₃ CH₂ — — cyclo- propyl A.1.26 Cl I CF₃ CHMe — — cyclo- propyl A.1.27 Cl I CF₃ CMe₂ — — cyclo- propyl A.1.28 Cl I CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.29 Br Cl CF₃ CH₂ — — cyclo- propyl A.1.30 Br Cl CF₃ CHMe — — cyclo- propyl A.1.31 Br Cl CF₃ CMe₂ — — cyclo- propyl A.1.32 Br Cl CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.33 Br Br CF CH₂ — — cyclo- propyl A.1.34 Br Br CF₃ CHMe — — cyclo- propyl A.1.35 Br Br CF₃ CMe₂ — — cyclo- propyl A.1.36 Br Br CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.37 Br F CF₃ CH₂ — — cyclo- propyl A.1.38 Br F CF₃ CHMe — — cyclo- propyl A.1.39 Br F CF₃ CMe₂ — — cyclo- propyl A.1.40 Br F CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.41 Br I CF₃ CH₂ — — cyclo- propyl A.1.42 Br I CF₃ CHMe — — cyclo- propyl A.1.43 Br I CF₃ CMe₂ — — cyclo- propyl A.1.44 Br I CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.45 Me Cl Cl CH₂ — — cyclo- propyl A.1.46 Me Cl Cl CHMe — — cyclo- propyl A.1.47 Me Cl Cl CMe₂ — — cyclo- propyl A.1.48 Me Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.49 Me Br Cl CH₂ — — cyclo- propyl A.1.50 Me Br Cl CHMe — — cyclo- propyl A.1.51 Me Br Cl CMe₂ — — cyclo- propyl A.1.52 Me Br Cl C(CH₂CH₂) — — cyclo- propyl A.1.53 Me F Cl CH₂ — — cyclo- propyl A.1.54 Me F Cl CHMe — — cyclo- propyl A.1.55 Me F Cl CMe₂ — — cyclo- propyl A.1.56 Me F Cl C(CH₂CH₂) — — cyclo- propyl A.1.57 Me I Cl CH₂ — — cyclo- propyl A.1.58 Me I Cl CHMe — — cyclo- propyl A.1.59 Me I Cl CMe₂ — — cyclo- propyl A.1.60 Me I Cl C(CH₂CH₂) — — cyclo- propyl A.1.61 Cl Cl Cl CH₂ — — cyclo- propyl A.1.62 Cl Cl Cl CHMe — — cyclo- propyl A.1.63 Cl Cl Cl CMe₂ — — cyclo- propyl A.1.64 Cl Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.65 Cl Br Cl CH₂ — — cyclo- propyl A.1.66 Cl Br Cl CHMe — — cyclo- propyl A.1.67 Cl Br Cl CMe₂ — — cyclo- propyl A.1.68 Cl Br Cl C(CH₂CH₂) — — cyclo- propyl A.1.69 Cl F Cl CH — — cyclo- propyl A.1.70 Cl F Cl CHMe — — cyclo- propyl A.1.71 Cl F Cl CMe₂ — — cyclo- propyl A.1.72 Cl F Cl C(CH₂CH₂) — — cyclo- propyl A.1.73 Cl I Cl CH₂ — — cyclo- propyl A.1.74 Cl I Cl CHMe — — cyclo- propyl A.1.75 Cl I Cl CMe₂ — — cyclo- propyl A.1.76 Cl I Cl C(CH₂CH₂) — — cyclo- propyl A.1.77 Br Cl Cl CH₂ — — cyclo- propyl A.1.78 Br Cl Cl CHMe — — cyclo- propyl A.1.79 Br Cl Cl CMe₂ — — cyclo- propyl A.1.80 Br Cl Cl C(CH₂CH₂) — — cyclo- propyl A.1.81 Br Br Cl CH₂ — — cyclo- propyl A.1.82 Br Br Cl CHMe — — cyclo- propyl A.1.83 Br Br Cl CMe₂ — — cyclo- propyl A.1.84 Br Br Cl C(CH₂CH₂) — — cyclo- propyl A.1.85 Br F Cl CH₂ — — cyclo- propyl A.1.86 Br F Cl CHMe — — cyclo- propyl A.1.87 Br F Cl CMe₂ — — cyclo- propyl A.1.88 Br F Cl C(CH₂CH₂) — — cyclo- propyl A.1.89 Br I Cl CH₂ — — cyclo- propyl A.1.90 Br I Cl CHMe — — cyclo- propyl A.1.91 Br I Cl CMe₂ — — cyclo- propyl A.1.92 Br I Cl C(CH₂CH₂) — — cyclo- propyl A.1.93 Me Cl Br CH₂ — — cyclo- propyl A.1.94 Me Cl Br CHMe — — cyclo- propyl A.1.95 Me Cl Br CMe₂ — — cyclo- propyl A.1.96 Me Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.97 Me Br Br CH₂ — — cyclo- propyl A.1.98 Me Br Br CHMe — — cyclo- propyl A.1.99 Me Br Br CMe₂ — — cyclo- propyl A.1.100 Me Br Br C(CH₂CH₂) — — cyclo- propyl A.1.101 Me F Br CH₂ — — cyclo- propyl A.1.102 Me F Br CHMe — — cyclo- propyl A.1.103 Me F Br CMe₂ — — cyclo- propyl A.1.104 Me F Br C(CH₂CH₂) — — cyclo- propyl A.1.105 Me I Br CH₂ — — cyclo- propyl A.1.106 Me I Br CHMe — — cyclo- propyl A.1.107 Me I Br CMe₂ — — cyclo- propyl A.1.108 Me I Br C(CH₂CH₂) — — cyclo- propyl A.1.109 Cl Cl Br CH₂ — — cyclo- propyl A.1.110 Cl Cl Br CHMe — — cyclo- propyl A.1.111 Cl Cl Br CMe₂ — — cyclo- propyl A.1.112 Cl Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.113 Cl Br Br CH₂ — — cyclo- propyl A.1.114 Cl Br Br CHMe — — cyclo- propyl A.1.115 Cl Br Br CMe₂ — — cyclo- propyl A.1.116 Cl Br Br C(CH₂CH₂) — — cyclo- propyl A.1.117 Cl F Br CH₂ — — cyclo- propyl A.1.118 Cl F Br CHMe — — cyclo- propyl A.1.119 Cl F Br CMe₂ — — cyclo- propyl A.1.120 Cl F Br C(CH₂CH₂) — — cyclo- propyl A.1.121 Cl I Br CH₂ — — cyclo- propyl A.1.122 Cl I Br CHMe — — cyclo- propyl A.1.123 Cl I Br CMe₂ — — cyclo- propyl A.1.124 Cl I Br C(CH₂CH₂) — — cyclo- propyl A.1.125 Br Cl Br CH₂ — — cyclo- propyl A.1.126 Br Cl Br CHMe — — cyclo- propyl A.1.127 Br Cl Br CMe₂ — — cyclo- propyl A.1.128 Br Cl Br C(CH₂CH₂) — — cyclo- propyl A.1.129 Br Br Br CH₂ — — cyclo- propyl A.1.130 Br Br Br CHMe — — cyclo- propyl A.1.131 Br Br Br CMe₂ — — cyclo- propyl A.1.132 Br Br Br C(CH₂CH₂) — — cyclo- propyl A.1.133 Br F Br CH₂ — — cyclo- propyl A.1.134 Br F Br CHMe — — cyclo- propyl A.1.135 Br F Br CMe₂ — — cyclo- propyl A.1.136 Br F Br C(CH₂CH₂) — — cyclo- propyl A.1.137 Br I Br CH₂ — — cyclo- propyl A.1.138 Br I Br CHMe — — cyclo- propyl A.1.139 Br I Br CMe₂ — — cyclo- propyl A.1.140 Br I Br C(CH₂CH₂) — — cyclo- propyl A.1.141 Me Cl OCHF₂ CH₂ — — cyclo- propyl A.1.142 Me Cl OCHF₂ CHMe — — cyclo- propyl A.1.143 Me Cl OCHF₂ CMe₂ — — cyclo- propyl A.1.144 Me Cl OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.145 Me Br OCHF₂ CH₂ — — cyclo- propyl A.1.146 Me Br OCHF₂ CHMe — — cyclo- propyl A.1.147 Me Br OCHF₂ CMe₂ — — cyclo- propyl A.1.148 Me Br OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.149 Me F OCHF₂ CH₂ — — cyclo- propyl A.1.150 Me F OCHF₂ CHMe — — cyclo- propyl A.1.151 Me F OCHF₂ CMe₂ — — cyclo- propyl A.1.152 Me F OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.153 Me I OCHF₂ CH₂ — — cyclo- propyl A.1.154 Me I OCHF₂ CHMe — — cyclo- propyl A.1.155 Me I OCHF₂ CMe₂ — — cyclo- propyl A.1.156 Me I OCHF₂ C(CH₂CH₂) — — cyclo propyl A.1.157 Cl Cl OCHF₂ CH₂ — — cyclo- propyl A.1.158 Cl Cl OCHF₂ CHMe — — cyclo- propyl A.1.159 Cl Cl OCHF₂ CMe₂ — — cyclo- propyl A.1.160 Cl Cl OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.161 Cl Br OCHF₂ CH₂ — — cyclo- propyl A.1.162 Cl Br OCHF₂ CHMe — — cyclo- propyl A.1.163 Cl Br OCHF₂ CMe₂ — — cyclo- propyl A.1.164 Cl Br OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.165 Cl F OCHF₂ CH₂ — — cyclo- propyl A.1.166 Cl F OCHF₂ CHMe — — cyclo- propyl A.1.167 Cl F OCHF₂ CMe₂ — — cyclo- propyl A.1.168 Cl F OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.169 Cl I OCHF₂ CH₂ — — cyclo- propyl A.1.170 Cl I OCHF₂ CHMe — — cyclo- propyl A.1.171 Cl I OCHF₂ CMe₂ — — cyclo- propyl A.1.172 Cl I OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.173 Br Cl OCHF₂ CH₂ — — cyclo- propyl A.1.174 Br Cl OCHF₂ CHMe — — cyclo- propyl A.1.175 Br Cl OCHF₂ CMe₂ — — cyclo- propyl A.1.176 Br Cl OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.177 Br Br OCHF₂ CH₂ — — cyclo- propyl A.1.178 Br Br OCHF₂ CHMe — — cyclo- propyl A.1.179 Br Br OCHF₂ CMe₂ — — cyclo- propyl A.1.180 Br Br OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.181 Br F OCHF₂ CH₂ — — cyclo- propyl A.1.182 Br F OCHF₂ CHMe — — cyclo- propyl A.1.183 Br F OCHF₂ CMe₂ — — cyclo- propyl A.1.184 Br F OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.185 Br I OCHF₂ CH₂ — — cyclo- propyl A.1.186 Br I OCHF₂ CHMe — — cyclo- propyl A.1.187 Br I OCHF₂ CMe₂ — — cyclo- propyl A.1.188 Br I OCHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.189 Me Cl OCH₂CF₃ CH₂ — — cyclo- propyl A.1.190 Me Cl OCH₂CF₃ CHMe — — cyclo- propyl A.1.191 Me Cl OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.192 Me Cl OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.193 Me Br OCH₂CF₃ CH₂ — — cyclo- propyl A.1.194 Me Br OCH₂CF₃ CHMe — — cyclo- propyl A.1.195 Me Br OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.196 Me Br OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.197 Me F OCH₂CF₃ CH₂ — — cyclo- propyl A.1.198 Me F OCH₂CF₃ CHMe — — cyclo- propyl A.1.199 Me F OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.200 Me F OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.201 Me I OCH₂CF₃ CH₂ — — cyclo- propyl A.1.202 Me I OCH₂CF₃ CHMe — — cyclo- propyl A.1.203 Me I OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.204 Me I OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.205 Cl Cl OCH₂CF₃ CH₂ — — cyclo- propyl A.1.206 Cl Cl OCH₂CF₃ CHMe — — cyclo- propyl A.1.207 Cl Cl OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.208 Cl Cl OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.209 Cl Br OCH₂CF₃ CH₂ — — cyclo- propyl A.1.210 Cl Br OCH₂CF₃ CHMe — — cyclo- propyl A.1.211 Cl Br OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.212 Cl Br OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.213 Cl F OCH₂CF₃ CH₂ — — cyclo- propyl A.1.214 Cl F OCH₂CF₃ CHMe — — cyclo- propyl A.1.215 Cl F OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.216 Cl F OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.217 Cl I OCH₂CF₃ CH₂ — — cyclo- propyl A.1.218 Cl I OCH₂CF₃ CHMe — — cyclo- propyl A.1.219 Cl I OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.220 Cl I OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.221 Br Cl OCH₂CF₃ CH₂ — — cyclo- propyl A.1.222 Br Cl OCH₂CF₃ CHMe — — cyclo- propyl A.1.223 Br Cl OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.224 Br Cl OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.225 Br Br OCH₂CF₃ CH₂ — — cyclo- propyl A.1.226 Br Br OCH₂CF₃ CHMe — — cyclo- propyl A.1.227 Br Br OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.228 Br Br OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.229 Br F OCH₂CF₃ CH₂ — — cyclo- propyl A.1.230 Br F OCH₂CF₃ CHMe — — cyclo- propyl A.1.231 Br F OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.232 Br F OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.233 Br I OCH₂CF₃ CH₂ — — cyclo- propyl A.1.234 Br I OCH₂CF₃ CHMe — — cyclo- propyl A.1.235 Br I OCH₂CF₃ CMe₂ — — cyclo- propyl A.1.236 Br I OCH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.237 Me Cl CHF₂ CH₂ — — cyclo- propyl A.1.238 Me Cl CHF₂ CHMe — — cyclo- propyl A.1.239 Me Cl CHF₂ CMe₂ — — cyclo- propyl A.1.240 Me Cl CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.241 Me Br CHF₂ CH₂ — — cyclo- propyl A.1.242 Me Br CHF₂ CHMe — — cyclo- propyl A.1.243 Me Br CHF₂ CMe₂ — — cyclo- propyl A.1.244 Me Br CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.245 Me F CHF₂ CH — — cyclo- propyl A.1.246 Me F CHF₂ CHMe — — cyclo- propyl A.1.247 Me F CHF₂ CMe₂ — — cyclo- propyl A.1.248 Me F CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.249 Me I CHF₂ CH₂ — — cyclo- propyl A.1.250 Me I CHF₂ CHMe — — cyclo- propyl A.1.251 Me I CHF₂ CMe₂ — — cyclo- propyl A.1.252 Me I CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.253 Cl Cl CHF₂ CH₂ — — cyclo- propyl A.1.254 Cl Cl CHF₂ CHMe — — cyclo- propyl A.1.255 Cl Cl CHF₂ CMe₂ — — cyclo- propyl A.1.256 Cl Cl CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.257 Cl Br CHF₂ CH₂ — — cyclo- propyl A.1.258 Cl Br CHF₂ CHMe — — cyclo- propyl A.1.259 Cl Br CHF₂ CMe₂ — — cyclo- propyl A.1.260 Cl Br CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.261 Cl F CHF₂ CH₂ — — cyclo- propyl A.1.262 Cl F CHF₂ CHMe — — cyclo- propyl A.1.263 Cl F CHF₂ CMe₂ — — cyclo- propyl A.1.264 Cl F CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.265 Cl I CHF₂ CH₂ — — cyclo- propyl A.1.266 Cl I CHF₂ CHMe — — cyclo- propyl A.1.267 Cl I CHF₂ CMe₂ — — cyclo- propyl A.1.268 Cl I CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.269 Br Cl CHF₂ CH₂ — — cyclo- propyl A.1.270 Br Cl CHF₂ CHMe — — cyclo- propyl A.1.271 Br Cl CHF₂ CMe₂ — — cyclo- propyl A.1.272 Br Cl CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.273 Br Br CHF₂ CH₂ — — cyclo- propyl A.1.274 Br Br CHF₂ CHMe — — cyclo- propyl A.1.275 Br Br CHF₂ CMe₂ — — cyclo- propyl A.1.276 Br Br CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.277 Br F CHF₂ CH₂ — — cyclo- propyl A.1.278 Br F CHF₂ CHMe — — cyclo- propyl A.1.279 Br F CHF₂ CMe — — cyclo- propyl A.1.280 Br F CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.281 Br I CHF₂ CH₂ — — cyclo- propyl A.1.282 Br I CHF₂ CHMe — — cyclo- propyl A.1.283 Br I CHF₂ CMe₂ — — cyclo- propyl A.1.284 Br I CHF₂ C(CH₂CH₂) — — cyclo- propyl A.1.285 Me Cl CH₂CF₃ CH₂ — — cyclo- propyl A.1.286 Me Cl CH₂CF₃ CHMe — — cyclo- propyl A.1.287 Me Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.288 Me Cl CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.289 Me Br CH₂CF₃ CH₂ — — cyclo- propyl A.1.290 Me Br CH₂CF₃ CHMe — — cyclo- propyl A.1.291 Me Br CH₂CF₃ CMe₂ — — cyclo- propyl A.1.292 Me Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.293 Me F CH₂CF₃ CH₂ — — cyclo- propyl A.1.294 Me F CH₂CF₃ CHMe — — cyclo- propyl A.1.295 Me F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.296 Me F CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.297 Me I CH₂CF₃ CH₂ — — cyclo- propyl A.1.298 Me I CH₂CF₃ CHMe — — cyclo- propyl A.1.299 Me I CH₂CF₃ CMe₂ — — cyclo- propyl A.1.300 Me I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.301 Cl Cl CH₂CF₃ CH₂ — — cyclo- propyl A.1.302 Cl Cl CH₂CF₃ CHMe — — cyclo- propyl A.1.303 Cl Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.304 Cl Cl CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.305 Cl Br CH₂CF₃ CH₂ — — cyclo- propyl A.1.306 Cl Br CH₂CF₃ CHMe — — cyclo- propyl A.1.307 Cl Br CH₂CF₃ CMe₂ — — cyclo- propyl A.1.308 Cl Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.309 Cl F CH₂CF₃ CH₂ — — cyclo- propyl A.1.310 Cl F CH₂CF₃ CHMe — — cyclo- propyl A.1.311 Cl F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.312 Cl F CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.313 Cl I CH₂CF₃ CH₂ — — cyclo- propyl A.1.314 Cl I CH₂CF₃ CHMe — — cyclo- propyl A.1.315 Cl I CH₂CF₃ CMe₂ — — cyclo- propyl A.1.316 Cl I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.317 Br Cl CH₂CF₃ CH₂ — — cyclo- propyl A.1.318 Br Cl CH₂CF₃ CHMe — — cyclo- propyl A.1.319 Br Cl CH₂CF₃ CMe₂ — — cyclo- propyl A.1.320 Br Cl CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.321 Br Br CH₂CF₃ CH₂ — — cyclo- propyl A.1.322 Br Br CH₂CF₃ CHMe — — cyclo- propyl A.1.323 Br Br CH₂CF₃ CMe₂ — — cyclo- propyl A.1.324 Br Br CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.325 Br F CH₂CF₃ CH₂ — — cyclo- propyl A.1.326 Br F CH₂CF₃ CHMe — — cyclo- propyl A.1.327 Br F CH₂CF₃ CMe₂ — — cyclo- propyl A.1.328 Br F CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.329 Br I CH₂CF₃ CH₂ — — cycJo- propyl A.1.330 Br I CH₂CF₃ CHMe — — cyclo- propyl A.1.331 Br I CH₂CF₃ CMe₂ — — cyclo- propyl A.1.332 Br I CH₂CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.333 Me Cl CF₃ CH₂ — — cyclo- propyl A.1.334 Me Cl CF₃ CHMe — — cyclo- propyl A.1.335 Me Cl CF₃ CHCF₃ — — cyclo- propyl A.1.336 Me Cl CF₃ CHEt — — cyclo- propyl A.1.337 Me Cl CF₃ CH(cyclo- — — cyclo- propyl) propyl A.1.338 Me Cl CF₃ CHnPr — — cyclo- propyl A.1.339 Me Cl CF₃ CHtBu — — cyclo- propyl A.1.340 Me Cl CF₃ CH(CH═CH₂) — — cyclo- propyl A.1.341 Me Cl CF₃ CH(CH═CH- — — cyclo- Me) propyl A.1.342 Me Cl CF₃ CH(CMe═CH₂) — — cyclo- propyl A.1.343 Me Cl CF₃ CH(CH₂CH═CH₂) — — cyclo- propyl A.1.344 Me Cl CF₃ CH(C═CH) — — cyclo- propyl A.1.345 Me Cl CF₃ CMe₂ — — cyclo- propyl A.1.346 Me Cl CF₃ CHCN — — cyclo- propyl A.1.347 Me Cl CF₃ CH(CH₂SMe) — — cyclo- propyl A.1.348 Me Cl CF₃ CH(CH₂S(O)₂Me) — — cyclo- propyl A.1.349 Me Cl CF₃ CH(CH₂OMe) — — cyclo- propyl A.1.350 Me Cl CF₃ CH(CH₂Cl) — — cyclo- propyl A.1.351 Me Cl CF₃ C(CH₂CH₂) — — cyclo- propyl A.1.352 Me Cl CF₃ C(CH₂CHF) — — cyclo- propyl A.1.353 Me Cl CF₃ C(CH₂CF₂) — — cyclo- propyl A.1.354 Me Cl CF₃ C(CH₂CHCl) — — cyclo- propyl A.1.355 Me Cl CF₃ C(CH₂CFCl) — — cyclo- propyl A.1.356 Me Cl CF₃ C(CH₂CCl₂) — — cyclo- propyl A.1.357 Me Cl CF₃ C(CH₂CHBr) — — cyclo- propyl A.1.358 Me Cl CF₃ C(CH₂CBr₂) — — cyclo- propyl A.1.359 Me Cl CF₃ C(CH₂CHMe) — — cyclo- propyl A.1.360 Me Cl CF₃ C(CH₂CMe₂) — — cyclo- propyl A.1.361 Me Cl CF₃ C(CH₂CHEt) — — cyclo- propyl A.1.362 Me Cl CF₃ C(CH₂CEt₂) — — cyclo- propyl A.1.363 Me Cl CF₃ CH₂CH₂ — — cyclo- propyl A.1.364 Me Cl CF₃ CH═CH — — cyclo- propyl A.1.365 Me Cl CF₃ CHMeCH₂ — — cyclo- propyl A.1.366 Me Cl CF₃ C(CH₂OCH₂) — — cyclo- propyl A.1.367 Me Cl CF₃ C(CH₂S(O)₂—CH₂) — — cyclo- propyl A.1.368 Me Cl CF₃ CH₂ O — cyclo- propyl A.1.369 Me Cl CF₃ CHMe O — cyclo- propyl A.1.370 Me Cl CF₃ CMe₂ O — cyclo- propyl A.1.371 Me Cl CF₃ C(CH₂CH₂) O — cyclo- propyl A.1.372 Me Cl CF₃ CHMe N-iso- — cyclo- propyl propyl A.1.373 Me Cl CF₃ CMe₂ N-iso- — cyclo- butyl propyl A.1.374 Me Cl CF₃ CH₂ NH — cyclo- propyl A.1.375 Me Cl CF₃ CHMe NMe — cyclo- propyl A.1.376 Me Cl CF₃ CMe₂ NEt — cyclo- propyl A.1.377 Me Cl CF₃ CH₂ O CH₂ cyclo- propyl A.1.378 Me Cl CF₃ CHMe O CH₂ cyclo- propyl A.1.379 Me Cl CF₃ CMe₂ O CH₂ cyclo- propyl A.1.380 Me Cl CF₃ C(CH₂CH₂) O CH₂ cyclo- propyl A.1.381 Me Cl CF₃ CHMe S(O) CH₂ cyclo- propyl A.1.382 Me Cl CF₃ CMe₂ S(O)₂ CH₂ cyclo- propyl A.1.383 Me Cl CF₃ CH₂ NH CH₂ cyclo- propyl A.1.384 Me Cl CF₃ CHMe NMe CH₂ cyclo- propyl A.1.385 Me Cl CF₃ CMe₂ NEt CH₂ cyclo- propyl A.1.386 Me Cl CF₃ CH₂ O CHMe cyclo- propyl A.1.387 Me Cl CF₃ CH₂ O CHCF₃ cyclo- propyl A.1.388 Me Cl CF₃ CH₂ O CHEt cyclo- propyl A.1.389 Me Cl CF₃ CH₂ O CH-(cyclo- cyclo- propyl) propyl A.1.390 Me Cl CF₃ CH₂ O CHnPr cyclo- propyl A.1.391 Me Cl CF₃ CH₂ O CHtBu cyclo- propyl A.1.392 Me Cl CF₃ CH₂ O CH(CH═CH₂) cyclo- propyl A.1.393 Me Cl CF₃ CH₂ O CH(CH═CHMe) cyclo- propyl A.1.394 Me Cl CF₃ CH₂ O CH—(CMe═CH₂) cyclo- propyl A.1.395 Me Cl CF₃ CH₂ O CH(CH₂CH═CH₂) cyclo- propyl A.1.396 Me Cl CF₃ CH₂ O CH(C═CH) cyclo- propyl A.1.397 Me Cl CF₃ CH₂ O CMe₂ cyclo- propyl A.1.398 Me Cl CF₃ CH₂ O CHCN cyclo- propyl A.1.399 Me Ci CF₃ CH₂ O CH(CH₂S-Me) cyclo- propyl A.1.400 Me Cl CF₃ CH₂ O CH(CH₂S—(O)₂Me) cyclo- propyl A.1.401 Me Cl CF₃ CH₂ O CH(CH₂O-Me) cyclo- propyl A.1.402 Me Cl CF₃ CH₂ O CH(CH₂Cl) cyclo- propyl A.1.403 Me Cl CF₃ CH₂ O C(CH₂CH₂) cyclo- propyl A.1.404 Me Cl CF₃ CH₂ O C(CH₂CHF) cyclo- propyl A.1.405 Me Cl CF₃ CH₂ O C(CH₂CF₂) cyclo- propyl A.1.406 Me Cl CF₃ CH₂ O C(CH₂CHCl) cyclo- propyl A.1.407 Me Cl CF₃ CH₂ O C(CH₂CFCl) cyclo- propyl A.1.408 Me Cl CF₃ CH₂ O C(CH₂CCl₂) cyclo- propyl A.1.409 Me Cl CF₃ CH₂ O C(CH₂CHBr) cyclo- propyl A.1.410 Me Cl CF₃ CH₂ O C(CH₂CBr₂) cyclo- propyl A.1.411 Me Cl CF₃ CH₂ O C(CH₂CHMe) cyclo- propyl A.1.412 Me Cl CF₃ CH₂ O C(CH₂CMe₂) cyclo- propyl A.1.413 Me Cl CF₃ CH₂ O C(CH₂CHEt) cyclo- propyl A.1.414 Me Cl CF₃ CH₂ O C(CH₂C-Et₂) cyclo- propyl A.1.415 Me Cl CF₃ CH₂ O CH₂CH₂ cyclo- propyl A.1.416 Me Cl CF₃ CH₂ O CH═CH cyclo- propyl A.1.417 Me Cl CF₃ CH₂ O CHMeCH₂ cyclo- propyl A.1.418 Me Cl CF₃ CH₂ — — 1-fluoro- cyclo- propyl A.1.419 Me Cl CF₃ CH₂ — — 1-chloro- cyclo- propyl A.1.420 Me Cl CF₃ CH₂ — — 1-bromo- cyclo- propyl A.1.421 Me Cl CF₃ CH₂ — — 1-methyl- cyclo- propyl A.1.422 Me Cl CF₃ CH₂ — — 1-ethyl- cyclo- propyl A.1.423 Me Cl CF₃ CH₂ — — 1-cyano- cyclo- propyl A.1.424 Me Cl CF₃ CH₂ — — 1-methyl- thiocyclo- propyl A.1.425 Me Cl CF₃ CH₂ — — 1- methoxy- cyclo- propyl A.1.426 Me Cl CF₃ CH₂ — — 1-hydroxy- cyclo- propyl A.1.427 Me Cl CF₃ CH₂ — — 1-trifluoro- methyl- cyclo- propyl A.1.428 Me Cl CF₃ CH₂ — — 2-fluoro- cyclo- propyl A.1.429 Me Cl CF₃ CH₂ — — 2,2- difluoro- cyclo- propyl A.1.430 Me Cl CF₃ CH₂ — — 2-chloro- cyclo- propyl A.1.431 Me Cl CF₃ CH₂ — — 2,2- dichloro- cyclo- propyl A.1.432 Me Cl CF₃ CH₂ — — 2-bromo- cyclo- propyl A.1.433 Me Cl CF₃ CH₂ — — 2,2- dibromo- cyclo- propyl A.1.434 Me Cl CF₃ CH₂ — — 2-chloro- 2-fluoro- cyclo- propyl A.1.435 Me Cl CF₃ CH₂ — — 2-methyl- cyclo- propyl A.1.436 Me Cl CF₃ CH₂ — — 2,2- dimethyl- cyclo- propyl A.1.437 Me Cl CF₃ CH₂ — — 2-ethyl- cyclo- propyl A.1.438 Me Cl CF₃ CH₂ — — 2,2- diethyl- cyclo- propyl A.1.439 Me Cl CF₃ CH₂ — — 2- cyanocyclo- propyl A.1.440 Me Cl CF₃ CH₂ — — 2-methyl- thiocyclo- propyl A.1.441 Me Cl CF₃ CH₂ — — 2- methoxy- cyclo- propyl A.1.442 Me Cl CF₃ CH₂ — — 2-hydroxy- cyclo- propyl A.1.443 Me Cl CF₃ CH₂ — — 2-trifluoro- methyl- cyclo- propyl A.1.444 Me Cl CF₃ CH₂ — — cyclo-butyl A.1.445 Me Cl CF₃ CH₂ — — 2-fluoro- cyclo-butyl A.1.446 Me Cl CF₃ CH₂ — — 2,2- difluoro- cyclo-butyl A.1.447 Me Cl CF₃ CH₂ — — 2-chloro- cyclo-butyl A.1.448 Me Cl CF₃ CH₂ — — 2,2- dichloro- cyclo-butyl A.1.449 Me Cl CF₃ CH₂ — — 2-bromo- cyclo-butyl A.1.450 Me Cl CF₃ CH₂ — — 2,2- dibromo- cyclo-butyl A.1.451 Me Cl CF₃ CH₂ — — 2-chloro- 2-fluoro- cyclo-butyl A.1.452 Me Cl CF₃ CH₂ — — 2-methyl- cyclo-butyl A.1.453 Me Cl CF₃ CH₂ — — 2,2- dimethyl- cyclo-butyl A.1.454 Me Cl CF₃ CH₂ — — 2-ethyl- cyclo-butyl A.1.455 Me Cl CF₃ CH₂ — — 2,2- diethyl- cyclo-butyl A.1.456 Me Cl CF₃ CH₂ — — 2-cyano- cyclo-butyl A.1.457 Me Cl CF₃ CH₂ — — 2-methyl- thiocyclo- butyl A.1.458 Me Cl CF₃ CH₂ — — 2- methoxy- cyclo-butyl A.1.459 Me Cl CF₃ CH₂ — — 2-hydroxy- cyclo-butyl A.1.460 Me Cl CF₃ CH₂ — — 2-trifluoro- methyl- cyclo-butyl A.1.461 Me Cl CF₃ CH₂ — — 3-methyl- cyclo-butyl A.1.462 Me Cl CF₃ CH₂ — — 3,3- dimethyl- cyclo-butyl A.1.463 Me Cl CF₃ CH₂ — — 3-chloro- cyclo-butyl A.1.464 Me Cl CF₃ CH₂ — — 3,3- dichloro- cyclo-butyl A.1.465 Me Cl CF₃ CHMe — — 1-fluoro- cyclo- propyl A.1.466 Me Cl CF₃ CHMe — — 1- chlorocyclo- propyl A.1.467 Me Cl CF₃ CHMe — — 1-bromo- cyclo- propyl A.1.468 Me Cl CF₃ CHMe — — 1-methyl- cyclo- propyl A.1.469 Me Cl CF₃ CHMe — — 1-ethyl- cyclo- propyl A.1.470 Me Cl CF₃ CHMe — — 1-cyano- cyclo- propyl A.1.471 Me Cl CF₃ CHMe — — 1-methyl- thiocyclo- propyl A.1.472 Me Cl CF₃ CHMe — — 1- methoxy- cyclo- propyl A.1.473 Me Cl CF₃ CHMe — — 1-hydroxy- cyclo- propyl A.1.474 Me Cl CF₃ CHMe — — 1-trifluoro- methyl- cyclo- propyl A.1.475 Me Cl CF₃ CHMe — — 2-fluoro- cyclo- propyl A.1.476 Me Cl CF₃ CHMe — — 2,2- difluoro- cyclo- propyl A.1.477 Me Cl CF₃ CHMe — — 2-chloro- cyclo- propyl A.1.478 Me Cl CF₃ CHMe — — 2,2- dichloro- cyclo- propyl A.1.479 Me Cl CF₃ CHMe — — 2-bromo- cyclo- propyl A.1.480 Me Cl CF₃ CHMe — — 2,2- dibromo- cyclo- propyl A.1.481 Me Cl CF₃ CHMe — — 2-chloro- 2-fluoro- cyclo- propyl A.1.482 Me Cl CF₃ CHMe — — 2-methyl- cyclo- propyl A.1.483 Me Cl CF₃ CHMe — — 2,2- dimethyl- cyclo- propyl A.1.484 Me Cl CF₃ CHMe — — 2-ethyl- cyclo- propyl A.1.485 Me Cl CF₃ CHMe — — 2,2- diethyl- cyclo- propyl A.1.486 Me Cl CF₃ CHMe — — 2-cyano- cyclo- pro pyl A.1.487 Me Cl CF₃ CHMe — — 2-methyl- thiocyclo- propyl A.1.488 Me Cl CF₃ CHMe — — 2- methoxy- cyclo- propyl A.1.489 Me Cl CF₃ CHMe — — 2-hydroxy- cyclo- propyl A.1.490 Me Cl CF₃ CHMe — — 2-trifluoro- methyl- cyclo- propyl A.1.491 Me Cl CF₃ CHMe — — cyclo-butyl A.1.492 Me Cl CF₃ CHMe — — 2-fluoro- cyclo-butyl A.1.493 Me Cl CF₃ CHMe — — 2,2- difluoro- cyclo-butyl A.1.494 Me Cl CF₃ CHMe — — 2- chlorocyclo- butyl A.1.495 Me Cl CF₃ CHMe — — 2,2- dichloro- cyclo-butyl A.1.496 Me Cl CF₃ CHMe — — 2-bromo- cyclo-butyl A.1.497 Me Cl CF₃ CHMe — — 2,2- dibromo- cyclo-butyl A.1.498 Me Cl CF₃ CHMe — — 2-chloro- 2-fluoro- cyclo-butyl A.1.499 Me Cl CF₃ CHMe — — 2-methyl- cyclo-butyl A.1.500 Me Cl CF₃ CHMe — — 2,2- dimethyl- cyclo-butyl A.1.501 Me Cl CF₃ CHMe — — 2-ethyl- cyclo-butyl A.1.502 Me Cl CF₃ CHMe — — 2,2- diethyl- cyclo-butyl A.1.503 Me Cl CF₃ CHMe — — 2- cyanocyclo- butyl A.1.504 Me Cl CF₃ CHMe — — 2-methyl- thiocyclo- butyl A.1.505 Me Cl CF₃ CHMe — — 2- methoxy- cyclo-butyl A.1.506 Me Cl CF₃ CHMe — — 2-hydroxy- cyclo-butyl A.1.507 Me Cl CF₃ CHMe — — 2-trifluoro- methyl- cyclo-butyl A.1.508 Me Cl CF₃ CHMe — — 3-methyl- cyclo-butyl A.1.509 Me Cl CF₃ CHMe — — 3,3- dimethyl- cyclo-butyl A.1.510 Me Cl CF₃ CHMe — — 3-chloro- cyclo-butyl A.1.511 Me Cl CF₃ CHMe — — 3,3- dichloro- cyclo-butyl A.1.512 Me Cl CF₃ CMe₂ — — 1-fluoro- cyclo- propyl A.1.513 Me Cl CF₃ CMe₂ — — 1-chloro- cyclo- propyl A.1.514 Me Cl CF₃ CMe₂ — — 1-bromo- cyclo- propyl A.1.515 Me Cl CF₃ CMe₂ — — 1-methyl- cyclo- propyl A.1.516 Me Cl CF₃ CMe₂ — — 1-ethyl- cyclo- propyl A.1.517 Me Cl CF₃ CMe₂ — — 1-cyano- cyclo- propyl A.1.518 Me Cl CF₃ CMe₂ — — 1-methyl- thiocyclo- propyl A.1.519 Me Cl CF₃ CMe₂ — — 1- methoxy- cyclo- propyl A.1.520 Me Cl CF₃ CMe₂ — — 1-hydroxy- cyclo- propyl A.1.521 Me Cl CF₃ CMe₂ — — 1-trifluoro- methyl- cyclo- propyl A.1.522 Me Cl CF₃ CMe₂ — — 2-fluoro- cyclo- propyl A.1.523 Me Cl CF₃ CMe₂ — — 2,2- difluoro- cyclo- propyl A.1.524 Me Cl CF₃ CMe₂ — — 2-chloro- cyclo- propyl A.1.525 Me Cl CF₃ CMe₂ — — 2,2- dichloro- cyclo- propyl A.1.526 Me Cl CF₃ CMe₂ — — 2-bromo- cyclo- propyl A.1.527 Me Cl CF₃ CMe₂ — — 2,2- dibromo- cyclo- propyl A.1.528 Me Cl CF₃ CMe₂ — — 2-chloro- 2-fluoro- cyclo- propyl A.1.529 Me Cl CF₃ CMe₂ — — 2-methyl- cyclo- propyl A.1.530 Me Cl CF₃ CMe₂ — — 2,2- dimethyl- cyclo- propyl A.1.531 Me Cl CF₃ CMe₂ — — 2-ethyl- cyclo- propyl A.1.532 Me Cl CF₃ CMe₂ — — 2,2- diethyl- cyclo- propyl A.1.533 Me Cl CF₃ CMe₂ — — 2-cyano- cyclo- propyl A.1.534 Me Cl CF₃ CMe₂ — — 2-methyl- thiocyclo- propyl A.1.535 Me Cl CF₃ CMe₂ — — 2- methoxy- cyclo- propyl A.1.536 Me Cl CF₃ CMe₂ — — 2-hydroxy- cyclo- propyl A.1.537 Me Cl CF₃ CMe₂ — — 2-trifluoro- methyl- cyclo- propyl A.1.538 Me Cl CF₃ CMe₂ — — cyclo-butyl A.1.539 Me Cl CF₃ CMe₂ — — 2-fluoro- cyclo-butyl A.1.540 Me Cl CF₃ CMe₂ — — 2,2- difluoro- cyclo-butyl A.1.541 Me Cl CF₃ CMe₂ — — 2-chloro- cyclo-butyl A.1.542 Me Cl CF₃ CMe₂ — — 2,2- dichloro- cyclo-butyl A.1.543 Me Cl CF₃ CMe₂ — — 2-bromo- cyclo-butyl A.1.544 Me Cl CF₃ CMe₂ — — 2,2- dibromo- cyclo-butyl A.1.545 Me Cl CF₃ CMe₂ — — 2-chloro- 2-fluoro- cyclo-butyl A.1.546 Me Cl CF₃ CMe₂ — — 2-methyl- cyclo-butyl A.1.547 Me Cl CF₃ CMe₂ — — 2,2- dimethyl- cyclo-butyl A.1.548 Me Cl CF₃ CMe₂ — — 2-ethyl- cyclo-butyl A.1.549 Me Cl CF₃ CMe₂ — — 2,2- diethyl- cyclo-butyl A.1.550 Me Cl CF₃ CMe₂ — — 2-cyano- cyclo-butyl A.1.551 Me Cl CF₃ CMe₂ — — 2-methyl- thiocyclo- butyl A.1.552 Me Cl CF₃ CMe₂ — — 2- methoxy- cyclo-butyl A.1.553 Me Cl CF₃ CMe₂ — — 2-hydroxy- cyclo-butyl A.1.554 Me Cl CF₃ CMe₂ — — 2-trifluoro- methyl- cyclo-butyl A.1.555 Me Cl CF₃ CMe₂ — — 3-methyl- cyclo-butyl A.1.556 Me Cl CF₃ CMe₂ — — 3,3- dimethyl- cyclo-butyl A.1.557 Me Cl CF₃ CMe₂ — — 3-chloro- cyclo-butyl A.1.558 Me Cl CF₃ CMe₂ — — 3,3- dichloro- cyclo-butyl A.1.559 Me Cl CF₃ CMe₂ — — 2-hydroxy- cyclo-butyl A.1.560 Me Cl CF₃ CMe₂ — — 2-trifluoro- methyl- cyclo-butyl A.1.561 Me Cl CF₃ CMe₂ — — 3-methyl- cyclo-butyl A.1.562 Me Cl CF₃ CMe₂ — — 3,3- dimethyl- cyclo-butyl A.1.563 Me Cl CF₃ CMe₂ — — 3-chloro- cyclo-butyl A.1.564 Me Cl CF₃ CMe₂ — — 3,3- dichloro- cyclo-butyl A.1.565 Me Cl CF₃ C(CH₂CH₂) — — 1-fluoro- cyclo- propyl A.1.566 Me Cl CF₃ C(CH₂CH₂) — — 1-chloro- cyclo- propyl A.1.567 Me Cl CF₃ C(CH₂CH₂) — — 1-bromo- cyclo- propyl A.1.568 Me Cl CF₃ C(CH₂CH₂) — — 1-methyl- cyclo- propyl A.1.569 Me Cl CF₃ C(CH₂CH₂) — — 1-ethyl- cyclo- propyl A.1.570 Me Cl CF₃ C(CH₂CH₂) — — 1-cyano- cyclo- propyl A.1.571 Me Cl CF₃ C(CH₂CH₂) — — 1-methyl- thiocyclo- propyl A.1.572 Me Cl CF₃ C(CH₂CH₂) — — 1- methoxy- cyclo- propyl A.1.573 Me Cl CF₃ C(CH₂CH₂) — — 1-hydroxy- cyclo- propyl A.1.574 Me Cl CF₃ C(CH₂CH₂) — — 1-trifluoro- methyl- cyclo- propyl A.1.575 Me Cl CF₃ C(CH₂CH₂) — — 2-fluoro- cyclo- propyl A.1.576 Me Cl CF₃ C(CH₂CH₂) — — 2,2- difluoro- cyclo- propyl A.1.577 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro- cyclo- propyl A.1.578 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dichloro- cyclo- propyl A.1.579 Me Cl CF₃ C(CH₂CH₂) — — 2-bromo- cyclo- propyl A.1.580 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dibromo- cyclo- propyl A.1.581 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro- 2-fluoro- cyclo- propyl A.1.582 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl- cyclo- propyl A.1.583 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dimethyl- cyclo- propyl A.1.584 Me Cl CF₃ C(CH₂CH₂) — — 2-ethyl- cyclo- propyl A.1.585 Me Cl CF₃ C(CH₂CH₂) — — 2,2- diethyl- cyclo- propyl A.1.586 Me Cl CF₃ C(CH₂CH₂) — — 2-cyano- cyclo- propyl A.1.587 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl- thiocyclo- propyl A.1.588 Me Cl CF₃ C(CH₂CH₂) — — 2- methoxy- cyclo- propyl A.1.589 Me Cl CF₃ C(CH₂CH₂) — — 2-hydroxy- cyclo- propyl A.1.590 Me Cl CF₃ C(CH₂CH₂) — — 2-trifluoro- methyl- cyclo- propyl A.1.591 Me Cl CF₃ C(CH₂CH₂) — — cyclo-butyl A1.592 Me Cl CF₃ C(CH₂CH₂) — — 2-fluoro- cyclo-butyl A1.593 Me Cl CF₃ C(CH₂CH₂) — — 2,2- difluoro- cyclo-butyl A1.594 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro- cyclo-butyl A1.595 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dichloro- cyclo-butyl A1.596 Me Cl CF₃ C(CH₂CH₂) — — 2-bromo- cyclo-butyl A1.597 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dibromo- cyclo-butyl A1.598 Me Cl CF₃ C(CH₂CH₂) — — 2-chloro- 2-fluoro- cyclo-butyl A1.599 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl- cyclo-butyl A1.600 Me Cl CF₃ C(CH₂CH₂) — — 2,2- dimethyl- cyclo-butyl A1.601 Me Cl CF₃ C(CH₂CH₂) — — 2-ethyl- cyclo-butyl A1.602 Me Cl CF₃ C(CH₂CH₂) — — 2,2- diethyl- cyclo-butyl A1.603 Me Cl CF₃ C(CH₂CH₂) — — 2-cyano- cyclo-butyl A1.604 Me Cl CF₃ C(CH₂CH₂) — — 2-methyl- thiocyclo- butyl A1.605 Me Cl CF₃ C(CH₂CH₂) — — 2- methoxy- cyclo-butyl A1.606 Me Cl CF₃ C(CH₂CH₂) — — 2-hydroxy- cyclo-butyl A1.607 Me Cl CF₃ C(CH₂CH₂) — — 2-trifluoro- methyl- cyclo-butyl A1.608 Me Cl CF₃ C(CH₂CH₂) — — 3-methyl- cyclo-butyl A1.609 Me Cl CF₃ C(CH₂CH₂) — — 3,3- dimethyl- cyclo-butyl A1.610 Me Cl CF₃ C(CH₂CH₂) — — 3-chloro- cyclo-butyl A1.611 Me Cl CF₃ C(CH₂CH₂) — — 3,3- dichloro- cyclo-butyl A1.612 Me Cl CF₃ CH₂ — — 1-methyl- 2,2- dichloro- cyclo- propyl A1.613 Me Cl CF₃ CH₂ — — 1-methyl- 2,2- dibromo- cyclo- propyl A1.614 Me Cl CF₃ CH₂ — — 2,2,3,3- tetrafluoro- cyclobutyl

FORMULATION EXAMPLES %=Percent by Weight

EXAMPLE F1 Emulsion concentrates a) b) c) Active ingredient 25% 40% 50% Calcium dodecylbenzenesulfonate 5% 8% 6% Castor oil polyethylene glycol ether (36 mol of EO) 5% — — Tributylphenoxypolyethylene glycol — 12% 4% ether (30 mol of EO) Cyclohexanone — 15% 20% Xylene mixture 65% 25% 20%

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

EXAMPLE F2 Solutions a) b) c) d) Active ingredient 80% 10% 5% 95% Ethylene glycol monomethyl ether 20% — — — Polyethylene glycol MW 400 — 70% — — N-Methylpyrrolid-2-one — 20% — — Epoxidized coconut oil — — 1%  5% Petroleum ether (boiling range: 160-190°) — — 94%  —

The solutions are suitable for use in the form of microdrops.

EXAMPLE F3 Granules a) b) c) d) Active ingredient  5% 10%  8% 21% Kaolin 94% — 79% 54% Highly disperse silica  1% — 13%  7% Attapulgite — 90% — 18%

The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier(s), and the solvent is subsequently evaporated in vacuo.

EXAMPLE F4 Dusts a) b) Active ingredient 2% 5% Highly disperse silica 1% 5% Talc 97%  — Kaolin — 90% 

Ready-to-use dusts are obtained by intimately mixing the carriers and the active ingredient.

EXAMPLE F5 Wettable powders a) b) c) Active ingredient 25%  50% 75% Sodium lignosulfonate 5%  5% — Sodium lauryl sulfate 3% —  5% Sodium —  6% 10% diisobutylnaphthalenesulfonate Octylphenoxypolyethylene glycol —  2% — ether (7-8 mol of EO) Highly disperse silica 5% 10% 10% Kaolin 62%  27% —

The active ingredient is mixed with the additives and the mixture is ground thoroughly in a suitable mill. This gives wettable powders, which can be diluted with water to give suspensions of any desired concentration.

EXAMPLE F6 Extruder granules Active ingredient 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 87%

The active ingredient is mixed with the additives, and the mixture is ground, moistened with water, extruded, granulated and dried in a stream of air.

EXAMPLE F7 Coated granules Active ingredient 3% Polyethylene glycol (MW 200) 3% Kaolin 94%

In a mixer, the finely ground active ingredient is applied uniformly to the kaolin, which has been moistened with the polyethylene glycol. This gives dust-free coated granules.

EXAMPLE F8 Suspension concentrate Active ingredient 40% Ethylene glycol 10% Nonylphenoxypolyethylene glycol ether (15 mol of EO)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1% 37% aqueous formaldehyde solution 0.2%  Silicone oil (75% aqueous emulsion) 0.8%  Water 32%

The finely ground active ingredient is mixed intimately with the additives. Suspensions of any desired concentration can be prepared from the thus resulting suspension concentrate by dilution with water.

The activity of the compositions according to the invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients. Suitable additions to active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

The following mixtures of the compounds of formula I with active ingredients are preferred (the abbreviation “TX” means “one compound selected from the group consisting of the compounds specifically described in tables P, P′ and A of the present invention”):

-   -   an adjuvant selected from the group of substances consisting of         petroleum oils (alternative name) (628)+TX,     -   an acaricide selected from the group of substances consisting of         1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,         2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts         name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC         name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name)         (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole         [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb         (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX,         amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX,         amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite         (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX,         AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,         azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX,         azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX,         benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX,         benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX,         bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate         (alternative name)+TX, bromocyclen (918)+TX, bromophos (920)+TX,         bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin         (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX,         butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC         name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX,         carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion         (947)+TX, CGA 50'439 (development code) (125)+TX, chinomethionat         (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX,         chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX,         chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulphide         (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX,         chloromebuform (977)+TX, chloromethiuron (978)+TX,         chloropropylate (983)+TX, chlorpyrifos (145)+TX,         chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I         (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine         (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos         (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos         (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX,         cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin         (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM         (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O         (1037)+TX, demephion-S (1037)+TX, demeton (1038)+TX,         demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl         (224)+TX, demeton-S (1038)+TX, demeton-S-methyl (224)+TX,         demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,         dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX,         dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol         (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox         (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)         (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton         (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6         [CCN]+TX, dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon         (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl         sulfone (IUPAC name) (1103)+TX, disulfuram (alternative name)         [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn         (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan         (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin         (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl         (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor         (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,         fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad         (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX,         fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX,         fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine         (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX,         fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX,         fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137         (development code) (1185)+TX, formetanate (405)+TX, formetanate         hydrochloride (405)+TX, formothion (1192)+TX, formparanate         (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox         (424)+TX, heptenophos (432)+TX, hexadecyl         cyclopropanecarboxylate (IUPAC/Chemical Abstracts name)         (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name)         (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl         O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,         ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,         jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX,         lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX,         mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative         name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX,         methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX,         methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX,         mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime         (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos         (561)+TX, morphothion (1300)+TX, moxidectin (alternative name)         [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512         (compound code)+TX, nifluridide (1309)+TX, nikkomycins         (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb         1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound         code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX,         oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX,         pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX,         petroleum oils (alternative name) (628)+TX, phenkapton         (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone         (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon         (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX,         polychloroterpenes (traditional name) (1347)+TX, polynactins         (alternative name) (653)+TX, proclonol (1350)+TX, profenofos         (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos         (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate         (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,         pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion         (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos         (711)+TX, quintiofos (1381)+TX, R-1492 (development code)         (1382)+TX, RA-17 (development code) (1383)+TX, rotenone         (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX,         selamectin (alternative name) [CCN]+TX, SI-0009 (compound         code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX,         spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,         sulfuram (alternative name) [CCN]+TX, sulfluramid (750)+TX,         sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code)         (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP         (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos         (777)+TX, tetradifon (786)+TX, tetranactin (alternative name)         (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX,         thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX,         thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX,         triamiphos (1441)+TX, triarathene (1443)+TX, triazophos         (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,         trifenofos (1455)+TX, trinactin (alternative name) (653)+TX,         vamidothion (847)+TX, vaniliprole [CCN] and yl-5302 (compound         code)+TX,     -   an algicide selected from the group of substances consisting of         bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX,         copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX,         dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX,         hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX,         quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate         (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name)         (347)+TX,     -   an anthelmintic selected from the group of substances consisting         of abamectin (1)+TX, crufomate (1011)+TX, doramectin         (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin         benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,         ivermectin (alternative name) [CCN]+TX, milbemycin oxime         (alternative name) [CCN]+TX, moxidectin (alternative name)         [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)         [CCN]+TX, spinosad (737) and thiophanate (1435)+TX,     -   an avicide selected from the group of substances consisting of         chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,         pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,     -   a bactericide selected from the group of substances consisting         of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,         4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)         (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX,         copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide         (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX,         dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf         (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative         name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride         hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC         name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX,         oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium         hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX,         streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,         tecloftalam (766)+TX, and thiomersal (alternative name)         [CCN]+TX,     -   a biological agent selected from the group of substances         consisting of Adoxophyes orana GV (alternative name) (12)+TX,         Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius         spp. (alternative name) (19)+TX, Anagrapha falcifera NPV         (alternative name) (28)+TX, Anagrus atomus (alternative name)         (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX,         Aphidius colemani (alternative name) (34)+TX, Aphidoletes         aphidimyza (alternative name) (35)+TX, Autographa californica         NPV (alternative name) (38)+TX, Bacillus firmus (alternative         name) (48)+TX, Bacillus sphaericus Neide (scientific name)         (49)+TX, Bacillus thuringiensis Berliner (scientific name)         (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name)         (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific         name) (51)+TX, Bacillus thuringiensis subsp. japonensis         (scientific name) (51)+TX, Bacillus thuringiensis subsp.         kurstaki (scientific name) (51)+TX, Bacillus thuringiensis         subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana         (alternative name) (53)+TX, Beauveria brongniartfii (alternative         name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,         Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia         pomonella GV (alternative name) (191)+TX, Dacnusa sibirica         (alternative name) (212)+TX, Diglyphus isaea (alternative name)         (254)+TX, Encarsia formosa (scientific name) (293)+TX,         Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa         zea NPV (alternative name) (431)+TX, Heterorhabditis         bacteriophora and H. megidis (alternative name) (433)+TX,         Hippodamia convergens (alternative name) (442)+TX, Leptomastix         dactylopii (alternative name) (488)+TX, Macrolophus caliginosus         (alternative name) (491)+TX, Mamestra brassicae NPV (alternative         name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX,         Metarhizium anisopliae var. acridum (scientific name) (523)+TX,         Metarhizium anisopliae var. anisopliae (scientific name)         (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV         (alternative name) (575)+TX, Orius spp. (alternative name)         (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX,         Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera         exigua multicapsid nuclear polyhedrosis virus (scientific name)         (741)+TX, Steinemema bibionis (alternative name) (742)+TX,         Steinernema carpocapsae (alternative name) (742)+TX, Steinernema         feltiae (alternative name) (742)+TX, Steinernema glaseri         (alternative name) (742)+TX, Steinernema riobrave (alternative         name) (742)+TX, Steinernema riobravis (alternative name)         (742)+TX, Steinernema scapterisci (alternative name) (742)+TX,         Steinernema spp. (alternative name) (742)+TX, Trichogramma spp.         (alternative name) (826)+TX, Typhlodromus occidentalis         (alternative name) (844) and Verticillium lecanii (alternative         name) (848)+TX,     -   a soil sterilant selected from the group of substances         consisting of iodomethane (IUPAC name) (542) and methyl bromide         (537)+TX,     -   a chemosterilant selected from the group of substances         consisting of apholate [CCN]+TX, bisazir (alternative name)         [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron         (250)+TX, dimatif (alternative name) (CCN)+TX, hemel (CCN)+TX,         hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl         apholate [CCN]+TX, morzid [CCN]+TX, penfluoron (alternative         name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name)         [CCN]+TX, thiotepa (alternative name) [CCN]+TX, tretamine         (alternative name) [CCN] and uredepa (alternative name)         [CCN]+TX,     -   an insect pheromone selected from the group of substances         consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol         (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name)         (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,         (E+TX, Z)-tetradeca-4+TX, 10-dien-1-yl acetate (IUPAC name)         (779)+TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX,         (Z)-hexadec-11-enal (IUPAC name) (436)+TX,         (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX,         (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,         (Z)-icos-13-en-10-one (IUPAC name) (448)+TX,         (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX,         (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,         (Z)-tetradec-9-en-11-yl acetate (IUPAC name) (784)+TX, (7E+TX,         9z)-dodeca-7+TX, 9-dien-1-yl acetate (IUPAC name) (283)+TX,         (9Z+TX, 11E)-tetradeca-9+TX, 11-dien-1-yl acetate (IUPAC name)         (780)+TX, (9Z+TX, 12E)-tetradeca-9+TX, 12-dien-1-yl acetate         (IUPAC name) (781)+TX, 14-methyloctadec-1-ene (IUPAC name)         (545)+TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (IUPAC         name) (544)+TX, alpha-multistriatin (alternative name) [CCN]+TX,         brevicomin (alternative name) (CCN)+TX, codlelure (alternative         name) [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure         (alternative name) (179)+TX, disparlure (277)+TX,         dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl         acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate         (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX,         ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol         (alternative name) [CCN]+TX, frontalin (alternative name)         [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure         (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II         (alternative name) (421)+TX, grandlure III (alternative name)         (421)+TX, grandlure IV (alternative name) (421)+TX, hexylure         [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol         (alternative name) [CCN]+TX, japonilure (alternative name)         (481)+TX, lineatin (alternative name) [CCN]+TX, litiure         (alternative name) [CCN]+TX, looplure (alternative name)         [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name)         [CCN]+TX, methyl eugenol (alternative name) (540)+TX, muscalure         (563)+TX, octadeca-2+TX, 13-dien-1-yl acetate (IUPAC name)         (588)+TX, octadeca-3+TX, 13-dien-1-yl acetate (IUPAC name)         (589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure         (alternative name) (317)+TX, ostramone (alternative name)         [CCN]+TX, sigiure [CCN]+TX, sordidin (alternative name)         (736)+TX, sulcatol (alternative name) [CCN]+TX,         tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure         (839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure         B, (alternative name) (839)+TX, trimedlure B₂ (alternative name)         (839)+TX, trimedlure C (alternative name) (839) and trunc-call         (alternative name) [CCN]+TX,     -   an insect repellent selected from the group of substances         consisting of 2-(octylthio)-ethanol (IUPAC name) (591)+TX,         butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX,         dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate         (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX,         diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl         phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide         [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide         [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX,     -   an insecticide selected from the group of substances consisting         of 1+TX, 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts         name) (1058)+TX, 1+TX, 1-dichloro-2+TX,         2-bis(4-ethylphenyl)ethane (IUPAC name) (1056)+TX, 1+TX,         2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,         1+TX, 2-dichloropropane with 1+TX, 3-dichloropropene (IUPAC         name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical         Abstracts name) (916)+TX, 2+TX, 2+TX, 2-trichloro-1-(3+TX,         4-dichlorophenyl)ethyl acetate (IUPAC name) (1451)+TX, 2+TX,         2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (IUPAC         name) (1066)+TX, 2-(1+TX, 3-dithiolan-2-yl)phenyl         dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX,         2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts         name) (935)+TX, 2-(4+TX, 5-dimethyl-1+TX, 3-dioxolan-2-yl)phenyl         methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX,         2-(4-chloro-3+TX, 5-xylyloxy)ethanol (IUPAC name) (986)+TX,         2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,         2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1+TX,         3-dione (IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl         methylcarbamate (IUPAC name) (1284)+TX, 2-thiocyanatoethyl         laurate (IUPAC name) (1433)+TX, 3-bromo-1-chloroprop-1-ene         (IUPAC name) (917)+TX, 3-methyl-1-phenylpyrazol-5-yl         dimethylcarbamate (IUPAC name) (1283)+TX,         4-methyl(prop-2-ynyl)amino-3+TX, 5-xylyl methylcarbamate (IUPAC         name) (1285)+TX, 5+TX, 5-dimethyl-3-oxocyclohex-1-enyl         dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX,         acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name)         [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile         (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX,         aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,         allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,         alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name)         [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX,         amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX,         amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine         (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ         60541 (compound code)+TX, azadirachtin (alternative name)         (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX,         azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus         thuringiensis delta endotoxins (alternative name) (52)+TX,         barium hexafluorosilicate (alternative name) [CCN]+TX, barium         polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin         [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408         (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb         (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX,         beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin         (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name)         (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX,         bioresmethrin (80)+TX, bis(2-chloroethyl)ether (IUPAC name)         (909)+TX, bistrifluoron (83)+TX, borax (86)+TX, brofenvalerate         (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen         (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos         (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX,         buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX,         butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim         (104)+TX, butylpyridaben (alternative name)+TX, cadusafos         (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,         calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,         carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX,         carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX,         carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion         (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap         hydrochloride (123)+TX, cevadine (alternative name) (725)+TX,         chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone         (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride         (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX,         chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos         (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX,         chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos         (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX,         chromafenozide (150)+TX, cinerin I (696)+TX, cinerin II         (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative         name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,         cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,         clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper         arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX,         coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX,         crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite         (alternative name) (177)+TX, CS 708 (development code)         (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX,         cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin         (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX,         cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine         (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene         (alternative name) [CCN]+TX, d-tetramethrin (alternative name)         (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX,         decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion         (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX, demeton         (1038)+TX, demetonmethyl (224)+TX, demeton-O (1038)+TX,         demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl         (224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron         (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon         (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX,         dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl         (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil         (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl         phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor         (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox         (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin         (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex         (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX,         dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX,         diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb         (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX,         dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative         name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name)         [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin         (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,         empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX,         endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane         (1124)+TX, eprinomectin (alternative name) [CCN]+TX,         esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX,         ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX,         ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate         (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX,         ethylene dibromide (316)+TX, ethylene dichloride (chemical name)         (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,         etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos         (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX,         fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion         (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb         (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX,         fenpyrad (alternative name)+TX, fensulfothion (1158)+TX,         fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate         (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide         (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,         flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil         (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX,         flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate         (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos         (1191)+TX, formetanate (405)+TX, formetanate hydrochloride         (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,         fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate         (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin         (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX,         guazatine (422)+TX, guazatine acetates (422)+TX, GY-81         (development code) (423)+TX, halfenprox (424)+TX, halofenozide         (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX,         heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron         (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen         cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,         imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb         (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX,         isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos         (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos         (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl         O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,         isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion         (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I         (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile         hormone I (alternative name) [CCN]+TX, juvenile hormone II         (alternative name) [CCN]+TX, juvenile hormone III (alternative         name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX,         lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin         (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos         (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl         methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide         (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX,         mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,         menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride         (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam         (519)+TX, metam-potassium (alternative name) (519)+TX,         metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos         (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts         name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX,         methocrotophos (1273)+TX, methomyl (531)+TX, methoprene         (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative         name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX,         methyl bromide (537)+TX, methyl isothiocyanate (543)+TX,         methylchloroform (alternative name) [CCN]+TX, methylene chloride         [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX,         metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate         (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative         name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,         monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin         (alternative name) [CCN]+TX, naftalofos (alternative name)         [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts         name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184         (compound code)+TX, nicotine (578)+TX, nicotine sulfate         (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine         (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride         complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250         (compound code)+TX, nornicotine (traditional name) (1319)+TX,         novaluron (585)+TX, noviflumuron (586)+TX,         O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC         name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl         phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl         O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name)         (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC         name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate         (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX,         oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT         (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,         parathion-methyl (616)+TX, penfluoron (alternative name)         [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate         (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils         (alternative name) (628)+TX, PH 60-38 (development code)         (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate         (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan         (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon         (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,         phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb         (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl         (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name)         (1346)+TX, polychloroterpenes (traditional name) (1347)+TX,         potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX,         prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX,         precocene II (alternative name) [CCN]+TX, precocene II         (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos         (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb         (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur         (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX,         prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine         (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin         (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,         pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX,         pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate         (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name)         [CCN]+TX, quinalphos (711)+TX, quinalphosmethyl (1376)+TX,         quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development         code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX,         resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development         code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania         (alternative name) (1387)+TX, ryanodine (traditional name)         (1387)+TX, sabadilla (alternative name) (725)+TX, schradan         (1389)+TX, sebufos (alternative name)+TX, selamectin         (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205         (compound code)+TX, SI-0404 (compound code)+TX, SI-0405         (compound code)+TX, silafluofen (728)+TX, SN 72129 (development         code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide         (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name)         (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium         pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name)         (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX,         spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX,         sulcofuron (746)+TX, sulcofuronsodium (746)+TX, sulfluramid         (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,         sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,         tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,         tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos         (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos         (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam         (alternative name)+TX, terbufos (773)+TX, tetrachloroethane         [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX,         theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox         (alternative name)+TX, thiamethoxam (792)+TX, thicrofos         (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX,         thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,         thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX,         thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin         (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin         (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX,         triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX,         triazuron (alternative name)+TX, trichlorfon (824)+TX,         trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat         (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,         trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,         vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX,         veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb         (854)+TX, yl-5302 (compound code)+TX, zeta-cypermethrin         (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide         (640)+TX, zolaprofos (1469) and ZXI 8901 (development code)         (858)+TX,     -   a molluscicide selected from the group of substances consisting         of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide         [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX,         copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin         (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde         (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX,         niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium         pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb         (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,         trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347)         and triphenyltin hydroxide (IUPAC name) (347)+TX,     -   a nematicide selected from the group of substances consisting of         AKD-3088 (compound code)+TX, 1+TX, 2-dibromo-3-chloropropane         (IUPAC/Chemical Abstracts name) (1045)+TX, 1+TX,         2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,         1+TX, 2-dichloropropane with 1+TX, 3-dichloropropene (IUPAC         name) (1063)+TX, 1+TX, 3-dichloropropene (233)+TX, 3+TX,         4-dichlorotetrahydrothiophene 1+TX, 1-dioxide (IUPAC/Chemical         Abstracts name) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine         (IUPAC name) (980)+TX, 5-methyl-6-thioxo-1+TX, 3+TX,         5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286)+TX,         6-isopentenylaminopurine (alternative name) (210)+TX, abamectin         (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb         (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX,         benclothiaz [CCN]+TX, benomyl (62)+TX, butylpyridaben         (alternative name)+TX, cadusafos (109)+TX, carbofuran (118)+TX,         carbon disulfide (945)+TX, carbosulfan (119)+TX, chloropicrin         (141)+TX, chlorpyrifos (145)+TX, cloethocarb (999)+TX,         cytokinins (alternative name) (210)+TX, dazomet (216)+TX, DBCP         (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX, dichlofenthion         (1051)+TX, dicliphos (alternative name)+TX, dimethoate (262)+TX,         doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,         emamectin benzoate (291)+TX, eprinomectin (alternative name)         [CCN]+TX, ethoprophos (312)+TX, ethylene dibromide (316)+TX,         fenamiphos (326)+TX, fenpyrad (alternative name)+TX,         fensulfothion (1158)+TX, fosthiazate (408)+TX, fosthietan         (1196)+TX, furfural (alternative name) [CCN]+TX, GY-81         (development code) (423)+TX, heterophos [CCN]+TX, iodomethane         (IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,         ivermectin (alternative name) [CCN]+TX, kinetin (alternative         name) (210)+TX, mecarphon (1258)+TX, metam (519)+TX,         metam-potassium (alternative name) (519)+TX, metam-sodium         (519)+TX, methyl bromide (537)+TX, methyl isothiocyanate         (543)+TX, milbemycin oxime (alternative name) [CCN]+TX,         moxidectin (alternative name) [CCN]+TX, Myrothecium verrucaria         composition (alternative name) (565)+TX, NC-184 (compound         code)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon         (639)+TX, phosphocarb [CCN]+TX, sebufos (alternative name)+TX,         selamectin (alternative name) [CCN]+TX, spinosad (737)+TX,         terbam (alternative name)+TX, terbufos (773)+TX,         tetrachlorothiophene (IUPAC/Chemical Abstracts name) (1422)+TX,         thiafenox (alternative name)+TX, thionazin (1434)+TX, triazophos         (820)+TX, triazuron (alternative name)+TX, xylenols [CCN]+TX,         yl-5302 (compound code) and zeatin (alternative name) (210)+TX,     -   a nitrification inhibitor selected from the group of substances         consisting of potassium ethylxanthate [CCN] and nitrapyrin         (580)+TX,     -   a plant activator selected from the group of substances         consisting of acibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX,         probenazole (658) and Reynoutria sachalinensis extract         (alternative name) (720)+TX,     -   a rodenticide selected from the group of substances consisting         of 2-isovalerylindan-1+TX, 3-dione (IUPAC name) (1246)+TX,         4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)         (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide         (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium         carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX,         bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide         (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX,         cholecalciferol (alternative name) (850)+TX, coumachlor         (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,         crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,         diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen         (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX,         flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH         (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name)         (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name)         (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX,         phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX,         phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite         (CCN)+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium         arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate         (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX,         warfarin (851) and zinc phosphide (640)+TX,     -   a synergist selected from the group of substances consisting of         2-(2-butoxyethoxy)-ethyl piperonylate (IUPAC name) (934)+TX,         5-(1+TX, 3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC         name) (903)+TX, farnesol with nerolidol (alternative name)         (324)+TX, MB-599 (development code) (498)+TX, MGK 264         (development code) (296)+TX, piperonyl butoxide (649)+TX,         piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (development         code) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and         sulfoxide (1406)+TX,     -   an animal repellent selected from the group of substances         consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper         naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon         (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine         (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX,         pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX,         trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram         (856)+TX,     -   a virucide selected from the group of substances consisting of         imanin (alternative name) [CCN] and ribavirin (alternative name)         [CCN]+TX,     -   and a wound protectant selected from the group of substances         consisting of mercuric oxide (512)+TX, octhilinone (590) and         thiophanate-methyl (802)+TX, the compound of formula A-1

the formula A-2

the formula A-3

the formula A-4

the formula A-5

the formula A-6

the formula A-7

the formula A-8

the formula A-9

the formula A-10

the formula A-11

the formula A-12

the formula A-13

the formula A-14

the formula A-15

the formula A-16

the formula A-17

the formula A-18

the formula A-19

the formula A-20

the formula A-21

the formula A-22

the formula A-23

the formula A-24

the formula A-25

the formula A-26

and Azaconazole (60207-31-0]+TX, Bitertanol [70585-36-3]+TX, Bromuconazole [116255-48-2]+TX, Cyproconazole [94361-06-5]+TX, Difenoconazole [119446-68-3]+TX, Diniconazole [83657-24-3]+TX, Epoxiconazole [106325-08-0]+TX, Fenbuconazole [114369-43-6]+TX, Fluquinconazole [136426-54-5]+TX, Flusilazole [85509-19-9]+TX, Flutriafol [76674-21-0]+TX, Hexaconazole [79983-71-4]+TX, Imazalil [35554-44-0]+TX, Imibenconazole [86598-92-7]+TX, Ipconazole [125225-28-7]+TX, Metconazole [125116-23-6]+TX, Myclobutanil [88671-89-0]+TX, Pefurazoate [101903-30-4]+TX, Penconazole [66246-88-6]+TX, Prothioconazole [178928-70-6]+TX, Pyrifenox [88283-41-4]+TX, Prochloraz [67747-09-5]+TX, Propiconazole [60207-90-1]+TX, Simeconazole [149508-90-7]+TX, Tebuconazole [107534-96-3]+TX, Tetraconazole [112281-77-3]+TX, Triadimefon [43121-43-3]+TX, Triadimenol [55219-65-3]+TX, Triflumizole [99387-89-0]+TX, Triticonazole [131983-72-7]+TX, Ancymidol [12771-68-5]+TX, Fenarimol [60168-88-9]+TX, Nuarimol [63284-71-9]+TX, Bupirimate [41483-43-6]+TX, Dimethirimol [5221-53-4]+TX, Ethirimol [23947-60-6]+TX, Dodemorph [1593-77-7]+TX, Fenpropidine [67306-00-7]+TX, Fenpropimorph [67564-91-4]+TX, Spiroxamine [118134-30-8]+TX, Tridemorph [81412-43-3]+TX, Cyprodinil [121552-61-2]+TX, Mepanipyrim [110235-47-7]+TX, Pyrimethanil [53112-28-0]+TX, Fenpiclonil [74738-17-3]+TX, Fludioxonil [131341-86-1]+TX, Benalaxyl [71626-11-4]+TX, Furalaxyl [57646-30-7]+TX, Metalaxyl [57837-19-1]+TX, R-Metalaxyl [70630-17-0]+TX, Ofurace [58810-48-3]+TX, Oxadixyl [77732-09-3]+TX, Benomyl [17804-35-2]+TX, Carbendazim [10605-21-7]+TX, Debacarb [62732-91-6]+TX, Fuberidazole [3878-19-1]+TX, Thiabendazole [148-79-8]+TX, Chlozolinate [84332-86-5]+TX, Dichlozoline [24201-58-9]+TX, Iprodione [36734-19-7]+TX, Myclozoline [54864-61-8]+TX, Procymidone [32809-16-8]+TX, Vinclozoline [50471-44-8]+TX, Boscalid [188425-85-6]+TX, Carboxin [5234-68-4]+TX, Fenfuram [24691-80-3]+TX, Flutolanil [66332-96-5]+TX, Mepronil [55814-41-0]+TX, Oxycarboxin [5259-88-1]+TX, Penthiopyrad [183675-82-3]+TX, Thifluzamide [130000-40-7]+TX, Guazatine [108173-90-6]+TX, Dodine [2439-10-3][112-65-2] (freie Base)+TX, Iminoctadine [13516-27-3]+TX, Azoxystrobin [131860-33-8]+TX, Dimoxystrobin [149961-52-4]+TX, Enestroburin {Proc. BCPC+TX, Int. Congr.+TX, Glasgow+TX, 2003+TX, 1+TX, 93}+TX, Fluoxastrobin [361377-29-9]+TX, Kresoxim-methyl [143390-89-0]+TX, Metominostrobin [133408-50-1]+TX, Trifloxystrobin [141517-21-7]+TX, Orysastrobin [248593-16-0]+TX, Picoxystrobin [117428-22-5]+TX, Pyraclostrobin [175013-18-0]+TX, Ferbam [14484-64-1]+TX, Mancozeb [8018-01-7]+TX, Maneb [12427-38-2]+TX, Metiram [9006-42-2]+TX, Propineb [12071-83-9]+TX, Thiram [137-26-8]+TX, Zineb [12122-67-7]+TX, Ziram [137-30-4]+TX, Captafol [2425-06-1]+TX, Captan [133-06-2]+TX, Dichlofluanid [1085-98-9]+TX, Fluoroimide [41205-21-4]+TX, Folpet [133-07-3]+TX, Tolylfluanid [731-27-1]+TX, Bordeaux Mixture [8011-63-0]+TX, Copperhydroxid [20427-59-2]+TX, Copperoxychlorid [1332-40-7]+TX, Coppersulfat [7758-98-7]+TX, Copperoxid [1317-39-1]+TX, Mancopper [53988-93-5]+TX, Oxine-copper [10380-28-6]+TX, Dinocap [131-72-6]+TX, Nitrothal-isopropyl [10552-74-6]+TX, Edifenphos [17109-49-8]+TX, lprobenphos [26087-47-8]+TX, Isoprothiolane [50512-35-1]+TX, Phosdiphen [36519-00-3]+TX, Pyrazophos [13457-18-6]+TX, Tolclofos-methyl [57018-04-9]+TX, Acibenzolar-5-methyl [135158-54-2]+TX, Anilazine [101-05-3]+TX, Benthiavalicarb [413615-35-7]+TX, Blasticidin-S [2079-00-7]+TX, Chinomethionat [2439-01-2]+TX, Chloroneb [2675-77-6]+TX, Chlorothalonil [1897-45-6]+TX, Cyflufenamid [180409-60-3]+TX, Cymoxanil [57966-95-7]+TX, Dichlone [117-80-6]+TX, Diclocymet [139920-32-4]+TX, Diclomezine [62865-36-5]+TX, Dicloran [99-30-9]+TX, Diethofencarb [87130-20-9]+TX, Dimethomorph [110488-70-5]+TX, SYP-LI90 (Flumorph) [211867-47-9]+TX, Dithianon [3347-22-6]+TX, Ethaboxam [162650-77-3]+TX, Etridiazole[2593-15-9]+TX, Famoxadone [131807-57-3]+TX, Fenamidone [161326-34-7]+TX, Fenoxanil [115852-48-7]+TX, Fentin [668-34-8]+TX, Ferimzone [89269-64-7]+TX, Fluazinam [79622-59-6]+TX, Fluopicolide [239110-15-7]+TX, Flusulfamide [106917-52-6]+TX, Fenhexamid [126833-17-8]+TX, Fosetyl-aluminium [39148-24-8]+TX, Hymexazol [10004-44-1]+TX, lprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid) [120116-88-3]+TX, Kasugamycin [6980-18-3]+TX, Methasulfocarb [66952-49-6]+TX, Metrafenone [220899-03-6]+TX, Pencycuron [66063-05-6]+TX, Phthalide [27355-22-2]+TX, Polyoxins [11113-80-7]+TX, Probenazole [27605-76-1]+TX, Propamocarb [25606-41-1]+TX, Proquinazid [189278-12-4]+TX, Pyroquilon [57369-32-1]+TX, Quinoxyfen [124495-18-7]+TX, Quintozene [82-68-8]+TX, Schwefel [7704-34-9]+TX, Tiadinil [223580-51-6]+TX, Triazoxide [72459-58-6]+TX, Tricyclazole [41814-78-2]+TX, Triforine [26644-46-2]+TX, Validamycin [37248-47-8]+TX, Zoxamide (RH7281) [156052-68-5]+TX, Mandipropamid [374726-62-2]+TX, the compound of formula F-1

wherein Ra₅ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX,; the compound of formula F-2

wherein Ra₆ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX,; the racemic compound of formula F-3 (syn)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the racemic mixture of formula F-4 (anti)

wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the compound of formula F-5

which is an epimeric mixture of racemic compounds of formulae F-3 (syn) and F-4 (anti), wherein the ratio from racemic compounds of formula F-3 (syn) to racemic cmpounds of formula F-4 (anti) is from 1000:1 to 1:1000 and wherein Ra₇ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the compound of formula F-6

wherein Ra₈ is trifluoromethyl or difluoromethyl (WO2004/035589)+TX, the racemic compound of formula F-7 (trans)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, the racemic compound of formula F-8 (cis)

wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, the compound of formula F-9

which is a mixture of the racemic compounds of formulae F-7 (trans) and F-8 (cis), wherein the ratio of the racemic compound of formula F-7 (trans) to the racemic compound of formula F-8 (cis) is 2:1 to 100:1; and wherein Ra₉ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, the compound of formula F-10

wherein R₁₀ is trifluoromethyl or difluoromethyl (WO2004/058723)+TX, the racemic compound of formula F-11 (trans)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, the racemic compound of formula F-12 (cis)

wherein R₁₁ is trifluoromethyl or difluoromethyl (WO03/074491)+TX, the compound of formula F-13

which is a racemic mixture of formulae F-11 (trans) and F-12 (cis), and wherein R₁₁ is trifluoromethyl or difluoromethyl (WO 03/074491)+TX, and the compound of formula F-14

(WO2004/058723)+TX, and the compound of formula F-15

The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The compounds of formulae A-1 to A-26 are described in WO 03/015518 or in WO 04/067528. The above described mixing partners are known. Where the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual—A World Compendium; Thirteenth Edition; Editor: C. D. S. Tomlin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound “abamectin” is described under entry number (1). Where “[CCN]” is added hereinabove to the particular compound, the compound in question is included in the “Compendium of Pesticide Common Names”, which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright© 1995-2004]; for example, the compound “acetoprole” is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred to hereinabove by a so-called “common name”, the relevant “ISO common name” or another “common name” being used in individual cases. If the designation is not a “common name”, the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemical name”, a “traditional name”, a “compound name” or a “development code” is used or, if neither one of those designations nor a “common name” is used, an “alternative name” is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.

The mixtures comprising a compound of formula I and one or more active ingredients as described above can be applied, for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and also in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the components (I) and active ingredients as described above is not essential for working the present invention.

BIOLOGICAL EXAMPLES %=Percent by Weight, Unless Otherwise Specified Example B1 Activity Against Aphis craccivora

Pea seedlings are infected with Aphis craccivora, subsequently sprayed with a spray mixture comprising 400 ppm of active ingredient and then incubated at 20°. 3 and 6 days later, the percentage reduction in the population (% activity) is determined by comparing the number of dead aphids between the treated and untreated plants. In this test, compounds listed in the Tables above show good activity.

Example B2 Activity Against Diabrotica balteata

Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after the spray coating has dried on, populated with 10 larvae (2nd instar) of Diabrotica balteata and introduced into a plastic container. 6 days later, the percentage reduction in the population (% activity) is determined by comparing the number of dead larvae between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity. In particular compounds P1, P2, P6, P7, P24, P29, P25, P60, P62, P63, P48, P46, P50, P23, P8, P66, P22, P14, P21, P11, P67, P68 have an activity of over 80%.

Example B3 Activity Against Heliothis virescens Foliar Application

Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after the spray coating has dried on, populated with 10 caterpillars (1st instar) of Heliothis virescens and introduced into a plastic container. 6 days later, the percentage reduction in the population and in the feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity. In particular compounds P1, P2, P6, P10, P3, P7, P15, P24, P51, P50, P63, P62, P61, P60, P12, P65, P66, P9, P8, P67, P68, P23, P21, P10, P11, P47, P52, P53 have an activity of over 80%.

Example B4 Activity Against Heliothis virescens Application to Eggs

Heliothis virescens eggs, which have been deposited on cotton, are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After 8 days, the percentage hatching rate of the eggs and the survival rate of the caterpillars (% activity) are evaluated in comparison with untreated control batches.

In this test, compounds listed in the Tables above show good activity. In particular compound P1, P2, P6, P7, P39, P3, P10, P24, P46, P48, P50, P51, P29, P31, P25, P67, P63, P62, P61, P60, P64, P68, P10, P8, P32, P9, P30, P23, P14, P21, P11, P40, P69, P70, P71, P72 have an activity of over 80%.

Example B5 Activity Against Myzus persicae Foliar Application

Pea seedlings are infected with Myzus persicae, subsequently sprayed with a spray mixture comprising 400 ppm of active ingredient and then incubated at 20°. 3 and 6 days later, the percentage reduction in the population (% activity) is determined by comparing the number of dead aphids between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.

Example B6 Activity Against Myzus Persicae Systemic Application

Pea seedlings are infected with Myzus persicae, and their roots are subsequently placed into a spray mixture comprising 400 ppm of active ingredient. The seedlings are then incubated at 20°. 3 and 6 days later, the percentage reduction in the population (% activity) is determined by comparing the number of dead aphids between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity.

Example B7 Activity Against Plutella xylostella

Young cabbage plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after the spray coating has dried on, populated with 10 caterpillars (3rd instar) of Plutella xylostella and introduced into a plastic container. 3 days later, the percentage reduction in the population and in the feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity. In particular compounds P1, P2, P6, P39, P3, P41, P7, P10, P15, P24, P29, P31, P25, P8, P9, P32, P30, P12, P13, P23, P22, P63, P62, P61, P60, P64, P63, P14, P46, P48, P50, P51, P17, P65, P66, P21, P18, P10, P67, P68, P16, P11, P35, P52, P53, P38, P40, P70 have an activity of over 80%.

Example B8 Activity Against Spodoptera littoralis

Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient and, after the spray coating has dried on, populated with 10 caterpillars (1st instar) of Spodoptera littoralis and introduced into a plastic container. 3 days later, the percentage reduction in the population and in the feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage between the treated and untreated plants.

In this test, compounds listed in the Tables above show good activity. In particular compounds P1, P2, P3, P6, P39, P41, P10, P63, P62, P61, P60, P64, P24, P7, P10, P67, P68, P29, P31, P25, P8, P32, P30, P9, P23, P14, P65, P66, P21, P11, P35, P34, P33, P38, P40, P69, P52, P53, P70 have an activity of over 80%.

Example B9 Activity Against Cydia

Standard Cydia diet cubes (1.5 cm width) are pierced with a tooth-pick and are immersed in liquid paraffin (ca. 80° C.). After the paraffin coat has hardened, an aqueous emulsion containing 400 ppm of active ingredient is applied using a De Vilbis sprayer (25 ml, 1 bar). After the spray coating has dried, the cubes are put into plastic containers which are then populated with two freshly hatched Cydia pomonella (1^(st) instar). The containers are then closed with a plastic cap. After 14 days incubation at 26° C. and 40-60% relative humidity, the survival rate of the caterpillars as well as their growth regulation is determined. In this test, compounds listed in the Tables above show good activity. In particular compounds P22, P6, P11, P65, P66, P17, P63, P62, P61, P60, P2, P3, P14, P67, P68, P15, P7, P21, P10, P24, P8, P13, P9, P23, P12 have an activity of over 80%.

Example B10 Comparison of the Insecticidal Activity of Compounds According to the Invention with the Structurally Most Closely Comparable Compound from the State of the Art (Compound No. 566 Described on Page 122 of WO03/024222)

(Compound No. P41 according to this invention)

(Cpd No. 566 According to the State of the Art)

B10a: Systemic Insecticide Test for Spodoptera littoralis (Cotton Leafworm):

Four day old maize seedlings (Zea mais, variety Stoneville) are placed individual in vials containing 24 ml water into which the chemical is diluted at the prescribed concentrations (12.5, 3 and 0.8 ppm). Seedlings are allowed to grow for six days. Subsequently leaves are cut and placed in a Petri dish (5 cm diameter), inoculated with twelve to fifteen 1st instar S. littoralis larvae and incubated for four days in a growth chamber (25° C., 50% r.h., 18:6 L:D photo period). Number of alive insects are counted and percentage of dead calculated. Tests were conducted with one replicate. Results are shown in Table B10a:

TABLE B10a Systemic Insecticide Test for Spodoptera littoralis Death rate (%) after 4 Compound: Concentration (ppm) days Comp. 566 (state of the art) 3 0 Comp. 566 (state of the art) 0.8 0 Comp. 566 (state of the art) 0.2 0 Comp. P41 (invention) 3 100 Comp. P41 (invention) 0.8 80 Comp. P41 (invention) 0.2 20

Table B10a shows that compound No. P41 according to the invention exerts a substantially better insecticidal action on Spodoptera littoralis than the compound from the state of the art. Especially at low application rates (3 and 0.8 ppm) the compound according to the invention is far superior to the compound of the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.

B10b: Insecticide Test for Heliothis virescens (Tobacco Budworm):

50-60 newly laid H. virescens eggs were placed on artificial diet in Petri dishes (5 cm diameter) and topically treated with 0.8 ml solution of compounds at the following rates: 3, 0.8, 0.2, 0.05. Petri dishes are maintained at 26±2° C., 50±10% r.h. in a dark room and assessment conducted one week after application (two replicates/treatment). Larvae mortality and effects on larvae growth were compared to the control. Results are shown in Table B10b:

TABLE B10 b Insecticide Test for Heliothis virescens Percent larvae showing growth Percent reduction Concentration larvae (compared Compound: (ppm) mortality to control) Comp. 566 (state 3 0 0 of the art) Comp. 566 (state 0.8 0 0 of the art) Comp. 566 (state 0.2 0 0 of the art) Comp. 566 (state 0.05 0 0 of the art) Comp. P41 (invention) 3 0 100 Comp. P41 (invention) 0.8 0 100 Comp. P41 (invention) 0.2 0 45 Comp. P41 (invention) 0.05 0 0

Table B10b shows that compound No. P41 according to the invention exerts a substantially better insecticidal action on Heliothis virescens than the compound from the state of the art. Especially at low application rates (3, 0.8 and 0.2 ppm) the compound according to the invention is far superior to the compound of the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds.

B10 c: Insecticide Test for Plutella xylostella (Diamond Back Moth):

Chinese cabbage plants were sprayed with insecticide at 3, 0.8, 0.2 and 0.05 ppm. Five cm diameter leaf disks were cut and placed in a Petri dish containing 6 ml agar (0.8%). Five P. xylostella larvae L3 were introduced into Petri dishes and kept at 26±2° C., 50±10% r.h. in a dark room (two replicates per treatment). Number of alive insects were counted and percentage of dead calculated after three days. Results are shown in Table B10c:

TABLE B10 c Insecticide Test for Plutella xylostella Death rate (%) after 5 Compound: Concentration (ppm) days Comp. 566 (state of the art) 3 25 Comp. 566 (state of the art) 0.8 5 Comp. 566 (state of the art) 0.2 10 Comp. 566 (state of the art) 0.05 0 Comp. P41 (invention) 3 60 Comp. P41 (invention) 0.8 80 Comp. P41 (invention) 0.2 0 Comp. P41 (invention) 0.05 0 Table B10c shows that compound No. P41 according to the invention exerts a substantially better insecticidal action on Plutella xylostella than the compound from the state of the art. Especially at low application rates (3 and 0.8 ppm) the compound according to the invention is far superior to the compound of the state of the art. This enhanced effect was not to be expected on the basis of the structural similarity of these compounds. 

1. A compound of formula I

wherein each of E and Z, which may be the same or different, represents oxygen or sulfur; A is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; and it being possible for the three- to ten-membered ring system itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃, —C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; X is oxygen, NH or C₁-C₄alkyl-N; Y is C₁-C₆alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, or a bivalent three- to ten-membered monocyclic or fused bicyclic ring system which can be partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms; and it being possible for the three- to ten-membered ring system itself and also for the C₁-C₆alkylene, C₂-C₆alkenylene and C₂-C₆alkynylene groups to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; p is 0 or 1; q is 0 or 1; B is a three- to four-membered ring system which is fully or partially saturated and can contain a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur, and it being possible for the three- to four-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen; each R₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkyl aminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁ independently is amino, formyl, C₂-C₆cyanoalkenyl, C₂-C₆alkylcarbonylamino, phenylcarbonylamino which can be mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁ independently is 2-,3- or 4-pyridylcarbonylamino which can be mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl; or each R₁ independently is C₂-C₆alkoxycarbonylamino, C₂-C₆alkylaminocarbonylamino, C₃-C₆dialkylaminocarbonylamino, C₂-C₆haloalkylcarbonyl or is a group R_(x)ON═C(R_(y))—, wherein R_(x) and R_(y) independently are hydrogen or C₁-C₆alkyl; n is 0, 1, 2, 3 or 4; each of R₂ and R₃, which may be the same or different, represents hydrogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl; or C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl or C₃-C₈cycloalkyl substituted by one or more substituents selected from halogen nitro, cyano, hydroxy, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino or C₁-C₆alkyl-C₃-C₆cycloalkylamino; D is phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl; or phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; or D is a group

R₄, R₄′, R₁₀, R₁₇, and R₁₉ independently from each other, are hydrogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₅, R₆, R₈, R₁₁, R₁₂, R₁₅, R₁₆ and R₁₈ independently from each other, are C₁-C₆alkyl or C₁-C₆alkyl mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₄alkoxy, C₂-C₄alkoxycarbonyl, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino or C₃-C₆cycloalkylamino; or are phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl; or are phenyl, 2-pyridyl, 3-pyridyl or 4-pyridyl mono-, di- or trisubstituted by C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, halogen, cyano, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₇, R₉, R₁₃ and R₁₄ independently from each other, are hydrogen, C₁-C₆alkyl, C₁-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkenyl or C₃-C₆haloalkenyl; and agronomically acceptable salts/isomers/enantiomers/tautomers/N-oxides of those compounds with the exception of the compound 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-methyl-6-(oxiranylmethyl-carbamoyl)-phenyl]-amide.
 2. A compound according to claim 1, wherein R₄′ is hydrogen and each R₁ independently is halogen, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl, phenyl, benzyl or phenoxy, or phenyl, benzyl or phenoxy mono-, di- or trisubstituted by halogen, cyano, nitro, halogen, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy or C₃-C₆-trialkylsilyl;
 3. A compound according to claim 1, wherein B is a three- to four-membered ring system which is fully or partially saturated, and it being possible for the three- to four-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl, or by a three- to ten-membered monocyclic or fused bicyclic ring system which can be aromatic, partially saturated or fully saturated and can contain 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, and it being possible for the three- to ten-membered ring system itself to be mono-, di- or trisubstituted by halogen, cyano, nitro, hydroxy, C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₆cycloalkyl, C₅-C₇cycloalkenyl, C₅-C₈cycloalkynyl, C₁-C₆haloalkyl, C₂-C₆haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆halocycloalkyl, C₅-C₇halocycloalkenyl, C₅-C₈halocycloalkynyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄haloalkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylamino, C₂-C₄dialkylamino, C₃-C₆cycloalkylamino, C₁-C₆alkyl-C₃-C₆cycloalkylamino, C₂-C₄alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₆dialkylaminocarbonyl, C₂-C₆alkoxycarbonyloxy, C₂-C₆alkylaminocarbonyloxy, C₃-C₆dialkylaminocarbonyloxy, C₃-C₆-trialkylsilyl or phenyl, it being possible for the phenyl group in turn to be substituted by hydroxy, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₁-C₃alkoxy-C₁-C₃alkylthio, C₂-C₄alkylcarbonyl-C₁-C₃alkylthio, C₂-C₄alkoxycarbonyl-C₁-C₃alkylthio, cyano-C₁-C₃alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆haloalkylsulfonyl, aminosulfonyl, C₁-C₂alkylaminosulfonyl, N,N-di(C₁-C₂alkyl)aminosulfonyl, di(C₁-C₄alkyl)amino, halogen, cyano or nitro; and substituents at nitrogen atoms in the ring systems being other than halogen.
 4. A compound according to claim 1, wherein A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene.
 5. A compound according to claim 1, wherein B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.
 6. A compound according to claim 1, wherein D is the group D₁.
 7. A pesticidal composition, which comprises at least one compound according to claim 1 of formula I or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.
 8. A composition according to claim 7 for controlling insects or representatives of the order Acarina.
 9. A method for controlling pests, which comprises applying a composition according to claim 6 to the pests or their environment.
 10. A method according to claim 9 for controlling insects or representatives of the order Acarina.
 11. A method according to claim 9 for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted.
 12. Plant propagation material treated in accordance with the method described in claim
 11. 13. A process for the preparation of a compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in salt form, which comprises a) for the preparation of a compound of formula I, in which R₂ is hydrogen and E and Z are oxygen, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula II

in which R₁, n, and D have the meanings given for formula I in claim 1, or, where appropriate, a tautomer and/or salt thereof with a compound of formula III HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III), in which R₃, A, X, Y, p, q and B have the meanings given for formula I, or, where appropriate, with a tautomer and/or salt thereof or, b) for the preparation of a compound of formula I, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula IV

in which R₁, R₂, n, Z and D have the meanings given for the formula I in claim 1; and X₁ is a leaving group, or, where appropriate, a tautomer and/or salt thereof with a compound of formula II HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III), in which R₃, A, X, Y, p, q and B have the meanings given for formula I, or, where appropriate, with a tautomer and/or salt thereof or, c) for the preparation of a compound of formula I, or, where appropriate, a tautomer and/or salt thereof, reacting a compound of formula V

in which R₁, R₂, R₃, n, A, X, Y, Z and B have the meanings given for the formula I in claim 1, or, where appropriate, a tautomer and/or salt thereof with a compound of formula VI X₂C(═O)D  (VI), in which D has the meaning given for formula I in claim 1; and X₂ is a leaving group, or, where appropriate, with a tautomer and/or salt thereof.
 14. A compound of formula V

wherein R₁, R₂, R₃, n, A, X, Y, Z and B have the meanings given for formula I in claim
 1. 15. A compound according to claim 14, wherein R₁ is C₁-C₄alkyl, halogen, C₁-C₅haloalkyl, nitro, C₁-C₄alkoxy, C₁-C₄-haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄haloalkylsulfinyl or C₁-C₄haloalkylsulfonyl; R₂ and R₃ are hydrogen; A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene; p and q are, independently from each other, 0 or 1; X is oxygen, NH; NCH₃ or NC₂H₅; Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy; B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂).
 16. A compound according to claim 15, wherein B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio.
 17. A compound of formula III HN(R₃)-A-(X)_(p)—(Y)_(q)—B  (III), in which R₃, A, X, Y, p, q and B have the meanings given for formula I in claim
 1. 18. A compound according to claim 17, wherein R₃ is hydrogen; A is C₁-C₆alkylene which may be substituted by C₃-C₆cycloalkyl, C₂-C₆alkenyl, cyano, C₁-C₄alkylthio, C₁-C₄alkylsulfonyl, C₁-C₄alkoxy, halogen or C₁-C₆haloalkyl; or A is C₃-C₆cycloalkylene; p and q are, independently from each other, 0 or 1; X is oxygen, NH; NCH₃ or NC₂H₅; Y is C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene or, C₁-C₄alkylene, C₂-C₆alkenylene or C₃-C₆alkinylene substituted by halogen, C₃-C₆cycloalkyl, C₁-C₄alkylsulfonyl or C₁-C₄alkoxy; B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio; or B is CH(CH₂O), CH(CHMeO), CH—(CMe₂O), CH(CH₂S), CH(CH₂OCH₂), CH(CHMeOCH₂), CH(CMe₂OCH₂), CH(CH₂S—(O)₂CH₂), CH(CHMeS(O)₂CH₂), CH(CMe₂S(O)₂CH₂), C(Me)-(CH₂O), C(Me)(CHMeO), C(Me)-(CMe₂O), C(Me)-(CH₂S), C(Me)-(CH₂OCH₂), C(Me)(CHMeOCH₂), C(Me)-(CMe₂OCH₂), C(Me)-(CH₂S(O)₂CH₂), C(Me)-(CHMe-S(O)₂CH₂) or C(Me)-(CMe₂-S(O)₂CH₂).
 19. A compound according to claim 18, wherein B is cyclopropyl or cyclobutyl which may be mono- di-, or trisubstituted by halogen, C₁-C₄alkyl, hydroxy, cyano, C₁-C₄alkoxy or C₁-C₄alkylthio. 